Crystal structure of bis-(2-methyl-1H-imidazol-3-ium) di-hydroxidobis(oxalato-κ(2) O (1),O (2))stannate(IV) monohydrate.

In the structure of the hydrated title salt, (C4H7N2)2[Sn(C2O4)2(OH)2]·H2O, the asymmetric unit comprises one stannate(IV) dianion, two organic cations and one water mol-ecule of crystallization. The [Sn(C2O4)2(OH)2](2-) dianion consists of an Sn(IV) atom chelated by two oxalate anions and coordinated by two OH(-) ligands in a cis octa-hedral arrangement. Neighbouring anions are connected through O-H⋯O hydrogen bonds between hydroxide groups and non-coordinating oxalate O atoms into layers expanding parallel to (100). In addition, cations and anions are linked through N-H⋯O hydrogen bonds, and the water mol-ecule bridges two anions with two O-H⋯O hydrogen bonds and is also the acceptor of an N-H⋯O hydrogen bond with one of the cations. Weak C-H⋯O hydrogen bonds are also observed. The intricate hydrogen bonding leads to the formation of a three-dimensional network.

Chemical context

Organotin(IV) compounds are a class of compounds studied for their numerous applications in various fields involving biological activities (Sirajuddin et al., 2014 ▸), biocidal properties (Davies et al., 2008 ▸) or catalysis applications (Meneghetti & Meneghetti, 2015 ▸). Inter­ested in tin(IV) chemistry, our group has so far synthesized and structurally characterized several compounds of this family, see, for example: Sarr et al. (2015 ▸); Diop et al. (2015 ▸); Gueye et al. (2014 ▸). In the course of designing new oxalatostannate(IV) complexes, we report here the result of the reaction between bis­(methyl-2-imidazolium) oxalate and SnCl2·2H2O that yielded the title compound (C4H7N2)2[Sn(C2O4)2(OH)2]·H2O with tin in oxidation state +IV. A similar oxidation of SnII to SnIV has been reported recently (Diop et al., 2015 ▸).

Structural commentary

The SnIV atom is chelated by two oxalate anions and is coordinated by two OH groups in a cis arrangement, leading to a distorted octa­hedral environment (Fig. 1 ▸). The Sn—O distances involving the oxalate anions [2.103 (2) (O1), 2.077 (2) (O2), 2.074 (2) (O5) and 2.114 (2) Å (O6)] are in the typical range reported for oxalatostannate(IV) anions (Sarr et al., 2015 ▸; Gueye et al., 2014 ▸). The Sn—O distances involving the OH groups [2.001 (2) (O9) and 1.973 (2) Å (O10)] are shorter by ca 0.1 Å. The distortion from the ideal octa­hedron is reflected by the trans angle O1—Sn—O10 of 169.11 (9)° involving one of the hydroxyl groups and the oxalate O1 atom. Within the oxalate ligands, the distances [C1—O1 1.296 (4), C2—O2 1.300 (4), C3—O6 1.290 (4), C4—O5 1.299 (4) Å] and [C2—O3 1.215 (4), C1—O4 1.223 (4), O7—C3 1.220 (4), O8—C4 1.212 (4) Å] are compatible with single C—O and double C=O bonds, respectively. Bond lengths and angles within the two bis­(2-methyl-1H-imidazol-3-ium) cations are in normal ranges.

Figure 1

The structure of the mol­ecular components in the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius and hydrogen bonds are shown as dashed lines.

Supra­molecular features

Each stannate dianion [Sn(C2O4)2(OH)2]2− is linked to two neighbouring anions through hydrox­yl(OH)⋯O hydrogen bonds involving the non-coordinating oxalate O atoms as acceptor groups. These inter­actions lead to the formation of layers extending parallel to (100). The cations inter­act with the anions via N—H⋯O hydrogen bonds (one bifurcated) whereby the non-coordinating oxalate O atoms again are the acceptor groups with the exception of one hydroxyl O atom (O9) as an acceptor (Table 1 ▸). The two hydroxyl groups are also acceptor groups of two (water)OH⋯O inter­actions, giving a total of nine hydrogen-bonding inter­actions per stannate dianion (Fig. 2 ▸). In addition to the dominant classical O—H⋯O and N—H⋯O inter­actions, weak C—H⋯O hydrogen bonds are also present in the structure (Table 1 ▸).

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O7i	0.86	2.00	2.835 (3)	163
O10—H10⋯O4ii	0.87	2.06	2.909 (3)	167
O11—H11A⋯O10	0.83 (2)	1.95 (2)	2.766 (4)	169 (5)
O11—H11B⋯O9iii	0.83 (2)	2.10 (2)	2.914 (4)	170 (7)
N1—H1⋯O3iv	0.88	1.97	2.793 (4)	156
N1—H1⋯O4iv	0.88	2.50	3.131 (3)	129
N2—H2⋯O9	0.88	1.90	2.742 (3)	160
N3—H3⋯O11	0.88	1.84	2.713 (4)	175
N4—H4⋯O8v	0.88	1.94	2.787 (4)	161
C5—H5A⋯O4	0.98	2.55	3.460 (4)	155
C7—H7⋯O2vi	0.95	2.39	3.327 (4)	169
C8—H8⋯O4ii	0.95	2.58	3.444 (4)	152
C12—H12⋯O5vii	0.95	2.33	3.232 (4)	159

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

Figure 2

A view of a central stannate dianion (ball-and-stick representation) surrounded by its hydrogen-bonded neighbours (stick representation), viz three cations, two water mol­ecules and four other stannate anions. Hydrogen bonds are displayed as black dotted lines and H atoms not involved in hydrogen bonding have been omitted for clarity.

Synthesis and crystallization

The title compound was obtained by reacting in methanol in a 2:1 ratio SnCl2·2H2O with bis­(methyl-2-imidazolium) oxalate. The latter was previously prepared in aqueous solution by mixing in a 2:1 ratio methyl-2-imidazole with oxalic acid and allowing the water to evaporate at 333 K. Slow solvent evaporation at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The coordinates of H atoms of the water mol­ecules and hy­droxy groups were obtained from a difference map and were refined using SADI and DFIX restraints (Sheldrick, 2015b ▸). All other H atoms were positioned geometrically (C—H = 0.95, 0.98 Å, N—H = 0.88 Å) and refined as riding with U iso(H) = xU eq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.

Table 2

Experimental details

Crystal data
Chemical formula	(C4H7N2)2[Sn(C2O4)2(H2O)2]·H2O
M r	512.99
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	110
a, b, c (Å)	20.1391 (13), 7.0651 (5), 13.4942 (9)
β (°)	106.582 (2)
V (Å3)	1840.2 (2)
Z	4
Radiation type	Ga Kα, λ = 1.34139 Å
μ (mm−1)	7.83
Crystal size (mm)	0.19 × 0.11 × 0.09
Data collection
Diffractometer	Bruker Venture Metaljet
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)
T min, T max	0.509, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	42907, 4235, 4110
R int	0.058
(sin θ/λ)max (Å−1)	0.651
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.040, 0.101, 1.07
No. of reflections	4235
No. of parameters	265
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)	1.87, −0.81

Computer programs: APEX2 and SAINT (Bruker, 2014 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸), OLEX2 (Dolomanov et al., 2009 ▸), Mercury (Macrae et al., 2008 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016002061/wm5268sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016002061/wm5268Isup2.hkl

CCDC reference: 1451548

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C4H7N2)2[Sn(C2O4)2(H2O)2]·H2O	F(000) = 1024
Mr = 512.99	Dx = 1.852 Mg m−3
Monoclinic, P21/c	Ga Kα radiation, λ = 1.34139 Å
a = 20.1391 (13) Å	Cell parameters from 9589 reflections
b = 7.0651 (5) Å	θ = 4.2–60.8°
c = 13.4942 (9) Å	µ = 7.83 mm−1
β = 106.582 (2)°	T = 110 K
V = 1840.2 (2) Å3	Block, clear light colourless
Z = 4	0.19 × 0.11 × 0.09 mm

Bruker Venture Metaljet diffractometer	4235 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	4110 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	Rint = 0.058
Detector resolution: 10.24 pixels mm-1	θmax = 60.9°, θmin = 2.0°
ω and φ scans	h = −26→26
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −8→9
Tmin = 0.509, Tmax = 0.752	l = −17→17
42907 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0612P)2 + 2.7674P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4235 reflections	Δρmax = 1.87 e Å−3
265 parameters	Δρmin = −0.81 e Å−3
4 restraints

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.

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.

	x	y	z	Uiso*/Ueq
Sn1	0.24060 (2)	0.62119 (3)	0.27535 (2)	0.02481 (10)
O1	0.22492 (11)	0.6762 (3)	0.11720 (17)	0.0312 (4)
O2	0.13386 (12)	0.5897 (3)	0.21916 (18)	0.0293 (5)
O3	0.04507 (12)	0.6473 (3)	0.07971 (18)	0.0330 (5)
O4	0.13911 (12)	0.7325 (3)	−0.02786 (17)	0.0347 (5)
O5	0.34706 (12)	0.6212 (3)	0.29967 (19)	0.0278 (5)
O6	0.25904 (10)	0.3368 (3)	0.24215 (18)	0.0280 (4)
O7	0.34600 (13)	0.1302 (3)	0.2613 (2)	0.0368 (6)
O8	0.43752 (11)	0.4264 (3)	0.3297 (2)	0.0347 (5)
O9	0.24047 (12)	0.9006 (3)	0.2994 (2)	0.0306 (5)
H9	0.2722	0.9540	0.2777	0.046*
O10	0.24113 (12)	0.5339 (3)	0.41448 (17)	0.0321 (5)
H10	0.2163	0.6085	0.4403	0.048*
C1	0.16053 (15)	0.6868 (4)	0.0632 (2)	0.0274 (6)
C2	0.10678 (17)	0.6380 (4)	0.1231 (2)	0.0273 (6)
C3	0.32352 (15)	0.2896 (4)	0.2648 (2)	0.0280 (6)
C4	0.37567 (15)	0.4559 (4)	0.3017 (2)	0.0275 (6)
N1	0.01942 (13)	1.1771 (4)	0.1086 (2)	0.0289 (5)
H1	−0.0115	1.2288	0.0559	0.043*
N2	0.11571 (14)	1.0703 (4)	0.2068 (2)	0.0299 (5)
H2	0.1597	1.0387	0.2303	0.045*
C5	0.12035 (18)	1.2002 (5)	0.0351 (3)	0.0343 (7)
H5A	0.1243	1.0864	−0.0043	0.051*
H5B	0.1667	1.2509	0.0683	0.051*
H5C	0.0928	1.2956	−0.0116	0.051*
C6	0.08607 (16)	1.1515 (4)	0.1151 (2)	0.0271 (6)
C7	0.00616 (19)	1.1103 (4)	0.1971 (3)	0.0332 (7)
H7	−0.0372	1.1110	0.2118	0.040*
C8	0.06634 (17)	1.0440 (5)	0.2585 (2)	0.0334 (6)
H8	0.0736	0.9893	0.3250	0.040*
N3	0.40483 (15)	0.0861 (4)	0.5690 (2)	0.0342 (6)
H3	0.3611	0.1160	0.5404	0.051*
N4	0.49720 (14)	−0.0750 (4)	0.6344 (2)	0.0306 (5)
H4	0.5252	−0.1712	0.6567	0.046*
C9	0.38714 (19)	−0.2637 (5)	0.5737 (3)	0.0390 (7)
H9A	0.4017	−0.3457	0.6346	0.059*
H9B	0.3941	−0.3298	0.5136	0.059*
H9C	0.3380	−0.2320	0.5604	0.059*
C10	0.42895 (17)	−0.0874 (5)	0.5925 (2)	0.0298 (6)
C11	0.45913 (19)	0.2124 (5)	0.5965 (3)	0.0380 (7)
H11	0.4562	0.3460	0.5881	0.046*
C12	0.5171 (2)	0.1116 (4)	0.6374 (3)	0.0347 (7)
H12	0.5628	0.1599	0.6633	0.042*
O11	0.26942 (14)	0.1609 (4)	0.4740 (2)	0.0406 (6)
H11A	0.258 (3)	0.267 (3)	0.449 (4)	0.074 (18)*
H11B	0.259 (4)	0.079 (6)	0.428 (4)	0.10 (2)*

	U11	U22	U33	U12	U13	U23
Sn1	0.01935 (13)	0.02397 (14)	0.02993 (14)	0.00241 (6)	0.00517 (9)	0.00129 (6)
O1	0.0245 (10)	0.0368 (11)	0.0333 (11)	−0.0011 (9)	0.0097 (8)	0.0009 (9)
O2	0.0236 (10)	0.0338 (11)	0.0311 (11)	0.0006 (9)	0.0088 (9)	0.0052 (9)
O3	0.0233 (11)	0.0407 (12)	0.0327 (11)	−0.0004 (9)	0.0043 (9)	0.0021 (9)
O4	0.0353 (12)	0.0380 (12)	0.0295 (11)	0.0011 (9)	0.0073 (9)	0.0035 (9)
O5	0.0205 (10)	0.0245 (11)	0.0389 (12)	0.0019 (7)	0.0092 (9)	0.0008 (8)
O6	0.0216 (10)	0.0263 (10)	0.0357 (11)	−0.0001 (8)	0.0075 (8)	−0.0016 (9)
O7	0.0286 (12)	0.0265 (12)	0.0561 (16)	0.0006 (8)	0.0136 (11)	−0.0043 (9)
O8	0.0218 (10)	0.0284 (10)	0.0524 (14)	0.0023 (9)	0.0080 (10)	0.0003 (10)
O9	0.0266 (12)	0.0241 (10)	0.0408 (12)	0.0015 (8)	0.0090 (9)	0.0010 (9)
O10	0.0329 (11)	0.0344 (12)	0.0297 (10)	0.0044 (9)	0.0100 (9)	0.0037 (9)
C1	0.0257 (14)	0.0237 (14)	0.0321 (14)	0.0011 (11)	0.0070 (11)	−0.0011 (11)
C2	0.0263 (15)	0.0241 (14)	0.0295 (14)	−0.0003 (10)	0.0046 (12)	−0.0011 (10)
C3	0.0250 (14)	0.0259 (14)	0.0335 (14)	−0.0011 (11)	0.0089 (11)	−0.0020 (11)
C4	0.0253 (14)	0.0256 (14)	0.0311 (14)	0.0012 (11)	0.0071 (11)	0.0005 (11)
N1	0.0238 (12)	0.0302 (13)	0.0311 (12)	0.0037 (10)	0.0055 (10)	0.0016 (10)
N2	0.0241 (12)	0.0287 (12)	0.0342 (13)	0.0026 (10)	0.0039 (10)	−0.0011 (11)
C5	0.0340 (16)	0.0342 (17)	0.0375 (16)	−0.0007 (13)	0.0146 (13)	−0.0016 (13)
C6	0.0242 (14)	0.0246 (13)	0.0324 (15)	0.0008 (11)	0.0077 (12)	−0.0019 (11)
C7	0.0300 (17)	0.0335 (17)	0.0377 (17)	0.0005 (12)	0.0122 (14)	−0.0001 (12)
C8	0.0378 (17)	0.0298 (16)	0.0319 (15)	−0.0003 (13)	0.0086 (13)	0.0019 (12)
N3	0.0305 (14)	0.0313 (13)	0.0377 (14)	0.0056 (11)	0.0048 (11)	−0.0020 (11)
N4	0.0262 (13)	0.0274 (12)	0.0360 (14)	0.0032 (11)	0.0052 (11)	−0.0020 (11)
C9	0.0348 (17)	0.0329 (17)	0.0463 (18)	−0.0007 (14)	0.0067 (14)	−0.0071 (14)
C10	0.0266 (15)	0.0309 (14)	0.0313 (15)	0.0035 (12)	0.0071 (12)	−0.0041 (12)
C11	0.0416 (18)	0.0270 (15)	0.0443 (18)	0.0000 (13)	0.0106 (15)	−0.0007 (13)
C12	0.0328 (17)	0.0324 (17)	0.0384 (17)	−0.0040 (12)	0.0092 (14)	−0.0029 (12)
O11	0.0375 (13)	0.0423 (13)	0.0409 (13)	0.0100 (11)	0.0095 (11)	0.0049 (12)

Sn1—O1	2.103 (2)	N2—C8	1.380 (4)
Sn1—O2	2.077 (2)	C5—H5A	0.9800
Sn1—O5	2.074 (2)	C5—H5B	0.9800
Sn1—O6	2.114 (2)	C5—H5C	0.9800
Sn1—O9	2.001 (2)	C5—C6	1.478 (4)
Sn1—O10	1.973 (2)	C7—H7	0.9500
O1—C1	1.296 (4)	C7—C8	1.342 (5)
O2—C2	1.300 (4)	C8—H8	0.9500
O3—C2	1.215 (4)	N3—H3	0.8800
O4—C1	1.223 (4)	N3—C10	1.324 (4)
O5—C4	1.299 (4)	N3—C11	1.378 (5)
O6—C3	1.290 (4)	N4—H4	0.8800
O7—C3	1.220 (4)	N4—C10	1.332 (4)
O8—C4	1.212 (4)	N4—C12	1.375 (4)
O9—H9	0.8616	C9—H9A	0.9800
O10—H10	0.8653	C9—H9B	0.9800
C1—C2	1.563 (4)	C9—H9C	0.9800
C3—C4	1.560 (4)	C9—C10	1.484 (5)
N1—H1	0.8800	C11—H11	0.9500
N1—C6	1.332 (4)	C11—C12	1.344 (5)
N1—C7	1.379 (4)	C12—H12	0.9500
N2—H2	0.8800	O11—H11A	0.831 (15)
N2—C6	1.339 (4)	O11—H11B	0.827 (16)
O1—Sn1—O6	86.86 (9)	C8—N2—H2	125.4
O2—Sn1—O1	79.01 (9)	H5A—C5—H5B	109.5
O2—Sn1—O6	92.69 (8)	H5A—C5—H5C	109.5
O5—Sn1—O1	90.55 (9)	H5B—C5—H5C	109.5
O5—Sn1—O2	166.65 (9)	C6—C5—H5A	109.5
O5—Sn1—O6	78.32 (8)	C6—C5—H5B	109.5
O9—Sn1—O1	88.58 (10)	C6—C5—H5C	109.5
O9—Sn1—O2	96.65 (9)	N1—C6—N2	107.1 (3)
O9—Sn1—O5	91.33 (8)	N1—C6—C5	126.3 (3)
O9—Sn1—O6	168.64 (9)	N2—C6—C5	126.6 (3)
O10—Sn1—O1	169.11 (9)	N1—C7—H7	126.6
O10—Sn1—O2	92.17 (9)	C8—C7—N1	106.8 (3)
O10—Sn1—O5	97.17 (9)	C8—C7—H7	126.6
O10—Sn1—O6	87.19 (9)	N2—C8—H8	126.4
O10—Sn1—O9	98.87 (10)	C7—C8—N2	107.2 (3)
C1—O1—Sn1	114.71 (19)	C7—C8—H8	126.4
C2—O2—Sn1	115.6 (2)	C10—N3—H3	125.5
C4—O5—Sn1	115.80 (18)	C10—N3—C11	109.1 (3)
C3—O6—Sn1	114.93 (19)	C11—N3—H3	125.5
Sn1—O9—H9	110.0	C10—N4—H4	125.3
Sn1—O10—H10	110.2	C10—N4—C12	109.4 (3)
O1—C1—C2	115.2 (3)	C12—N4—H4	125.3
O4—C1—O1	126.1 (3)	H9A—C9—H9B	109.5
O4—C1—C2	118.7 (3)	H9A—C9—H9C	109.5
O2—C2—C1	114.7 (3)	H9B—C9—H9C	109.5
O3—C2—O2	125.1 (3)	C10—C9—H9A	109.5
O3—C2—C1	120.2 (3)	C10—C9—H9B	109.5
O6—C3—C4	114.9 (3)	C10—C9—H9C	109.5
O7—C3—O6	126.1 (3)	N3—C10—N4	107.7 (3)
O7—C3—C4	119.0 (3)	N3—C10—C9	125.8 (3)
O5—C4—C3	114.6 (2)	N4—C10—C9	126.5 (3)
O8—C4—O5	124.8 (3)	N3—C11—H11	126.4
O8—C4—C3	120.6 (3)	C12—C11—N3	107.3 (3)
C6—N1—H1	125.2	C12—C11—H11	126.4
C6—N1—C7	109.7 (3)	N4—C12—H12	126.7
C7—N1—H1	125.2	C11—C12—N4	106.6 (3)
C6—N2—H2	125.4	C11—C12—H12	126.7
C6—N2—C8	109.2 (3)	H11A—O11—H11B	110 (3)
Sn1—O1—C1—O4	173.7 (3)	O7—C3—C4—O8	−2.5 (5)
Sn1—O1—C1—C2	−5.5 (3)	N1—C7—C8—N2	−0.2 (4)
Sn1—O2—C2—O3	−172.4 (2)	C6—N1—C7—C8	0.4 (4)
Sn1—O2—C2—C1	7.4 (3)	C6—N2—C8—C7	0.0 (4)
Sn1—O5—C4—O8	−168.6 (3)	C7—N1—C6—N2	−0.4 (4)
Sn1—O5—C4—C3	11.0 (3)	C7—N1—C6—C5	178.5 (3)
Sn1—O6—C3—O7	172.8 (3)	C8—N2—C6—N1	0.2 (4)
Sn1—O6—C3—C4	−6.1 (3)	C8—N2—C6—C5	−178.7 (3)
O1—C1—C2—O2	−1.2 (4)	N3—C11—C12—N4	−0.1 (4)
O1—C1—C2—O3	178.6 (3)	C10—N3—C11—C12	0.0 (4)
O4—C1—C2—O2	179.6 (3)	C10—N4—C12—C11	0.2 (4)
O4—C1—C2—O3	−0.7 (4)	C11—N3—C10—N4	0.1 (4)
O6—C3—C4—O5	−3.2 (4)	C11—N3—C10—C9	−179.0 (3)
O6—C3—C4—O8	176.5 (3)	C12—N4—C10—N3	−0.2 (4)
O7—C3—C4—O5	177.8 (3)	C12—N4—C10—C9	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O7i	0.86	2.00	2.835 (3)	163
O10—H10···O4ii	0.87	2.06	2.909 (3)	167
O11—H11A···O10	0.83 (2)	1.95 (2)	2.766 (4)	169 (5)
O11—H11B···O9iii	0.83 (2)	2.10 (2)	2.914 (4)	170 (7)
N1—H1···O3iv	0.88	1.97	2.793 (4)	156
N1—H1···O4iv	0.88	2.50	3.131 (3)	129
N2—H2···O9	0.88	1.90	2.742 (3)	160
N3—H3···O11	0.88	1.84	2.713 (4)	175
N4—H4···O8v	0.88	1.94	2.787 (4)	161
C5—H5A···O4	0.98	2.55	3.460 (4)	155
C7—H7···O2vi	0.95	2.39	3.327 (4)	169
C8—H8···O4ii	0.95	2.58	3.444 (4)	152
C12—H12···O5vii	0.95	2.33	3.232 (4)	159