μ-Squarato-κO:O-bis-{[2-(2-amino-ethyl)pyridine-κN,N']aqua-nickel(II)} squarate 0.25-hydrate.

The asymmetric unit of title compound, [Ni(2)(C(4)O(4))(C(7)H(10)N(2))(4)(H(2)O)(2)]C(4)O(4)·0.25H(2)O, contains one-half of a squarate ligand, one-half of an uncoordinated squarate dianion, two 2-(2-amino-ethyl)pyridine ligands and one aqua ligand, all coordinated to an Ni(II) ion. The compound also contains 0.25 solvent water mol-ecules. The Ni(II) ion has distorted octa-hedral geometry. The squarate ligand adopts a μ-1,2 coordination mode, the intra-dimer Ni(II)⋯Ni(II) separation being 7.1442 (7) Å, while the other squarate unit acts as a counter-anion. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen-bond inter-actions, forming a three-dimensional network.

Related literature

For general background, see: Bernardinelli et al. (1989 ▶); Bulut et al. (2004 ▶); Castro et al. (1995 ▶, 1997 ▶); Crispini et al. (2000 ▶); Kirchmaier et al. (2003 ▶); Lee et al. (1996 ▶); Milet et al. (2003 ▶); Solans et al. (1990 ▶); Spek (2003 ▶); Trombe et al. (2002 ▶); Uçar (2008 ▶); Uçar et al. (2006 ▶, 2007 ▶); Yang et al. (2003 ▶).

Experimental

Crystal data

[Ni2(C4O4)(C7H10N2)4(H2O)2]C4O4·0.25H2O

M = 870.16

Monoclinic,

a = 28.037 (3) Å

b = 8.0409 (5) Å

c = 17.7752 (16) Å

β = 103.572 (7)°

V = 3895.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.03 mm−1

T = 297 (2) K

0.3 × 0.2 × 0.1 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.49, T max = 0.81

12243 measured reflections

3809 independent reflections

3148 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.03

3809 reflections

282 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030808/pk2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030808/pk2116Isup2.hkl

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

[Ni2(C4O4)(C7H10N2)4(H2O)2]C4O4·0.25H2O	F(000) = 1816
Mr = 870.16	Dx = 1.484 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 24222 reflections
a = 28.037 (3) Å	θ = 1.7–28.0°
b = 8.0409 (5) Å	µ = 1.03 mm−1
c = 17.7752 (16) Å	T = 297 K
β = 103.572 (7)°	Prism, blue
V = 3895.3 (5) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Stoe IPDS-II diffractometer	3809 independent reflections
Radiation source: fine-focus sealed tube	3148 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.4°
ω scans	h = −34→34
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.49, Tmax = 0.81	l = −21→21
12243 measured reflections

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) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.9229P] where P = (Fo2 + 2Fc2)/3
3809 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.01456 (9)	0.6924 (3)	0.42515 (16)	0.0615 (6)
H1	0.0078	0.6622	0.3732	0.074*
C2	−0.02378 (11)	0.7007 (4)	0.4607 (2)	0.0880 (9)
H2	−0.0557	0.6790	0.4331	0.106*
C3	−0.01433 (14)	0.7411 (5)	0.5371 (3)	0.1052 (12)
H3	−0.0396	0.7486	0.5627	0.126*
C4	0.03335 (14)	0.7707 (4)	0.5755 (2)	0.0885 (10)
H4	0.0406	0.7952	0.6281	0.106*
C5	0.07099 (10)	0.7643 (3)	0.53672 (15)	0.0568 (6)
C6	0.12298 (10)	0.7973 (3)	0.57849 (13)	0.0590 (6)
H6A	0.1253	0.7886	0.6337	0.071*
H6B	0.1311	0.9109	0.5679	0.071*
C7	0.16091 (9)	0.6827 (3)	0.55784 (13)	0.0535 (5)
H7A	0.1905	0.6846	0.5990	0.064*
H7B	0.1485	0.5697	0.5529	0.064*
C8	0.18856 (8)	0.9557 (3)	0.32778 (14)	0.0528 (5)
H8	0.1919	1.0099	0.3749	0.063*
C9	0.21215 (9)	1.0213 (3)	0.27497 (17)	0.0667 (7)
H9	0.2311	1.1169	0.2865	0.080*
C10	0.20735 (10)	0.9436 (3)	0.20518 (17)	0.0685 (7)
H10	0.2223	0.9864	0.1679	0.082*
C11	0.17984 (9)	0.8010 (3)	0.19165 (14)	0.0586 (6)
H11	0.1759	0.7462	0.1445	0.070*
C12	0.15786 (8)	0.7380 (2)	0.24758 (12)	0.0445 (4)
C13	0.13096 (9)	0.5757 (3)	0.23578 (13)	0.0539 (5)
H13A	0.1395	0.5175	0.1929	0.065*
H13B	0.0960	0.5978	0.2216	0.065*
C14	0.14211 (8)	0.4629 (2)	0.30683 (13)	0.0498 (5)
H14A	0.1344	0.3488	0.2908	0.060*
H14B	0.1768	0.4686	0.3313	0.060*
C15	0.02527 (7)	0.9053 (2)	0.27139 (11)	0.0361 (4)
C16	0.02560 (8)	1.0864 (2)	0.27195 (12)	0.0452 (5)
C17	0.24949 (7)	0.8704 (2)	0.01973 (11)	0.0375 (4)
C18	0.21239 (7)	0.7408 (2)	−0.00476 (11)	0.0375 (4)
N1	0.06135 (7)	0.7253 (2)	0.46111 (11)	0.0472 (4)
N2	0.17263 (6)	0.7340 (2)	0.48476 (10)	0.0404 (4)
N3	0.16111 (6)	0.81826 (19)	0.31494 (9)	0.0396 (4)
N4	0.11369 (7)	0.51155 (19)	0.36278 (11)	0.0407 (4)
O1	0.05537 (5)	0.79065 (16)	0.29572 (8)	0.0449 (3)
O2	0.05610 (6)	1.19590 (18)	0.29910 (11)	0.0663 (5)
O3	0.24837 (5)	1.01589 (15)	0.04408 (9)	0.0487 (4)
O4	0.16716 (5)	0.73117 (15)	−0.01038 (9)	0.0470 (3)
O5	0.10943 (6)	1.01843 (17)	0.41638 (11)	0.0479 (4)
O6	0.0000	0.4863 (13)	0.2500	0.121 (6)	0.25
Ni1	0.114036 (8)	0.76294 (2)	0.391260 (13)	0.03314 (8)
H5A	0.1284 (10)	1.079 (3)	0.4454 (16)	0.062 (8)*
H5B	0.0958 (10)	1.073 (3)	0.3792 (16)	0.062 (8)*
H2A	0.1897 (8)	0.829 (3)	0.4946 (13)	0.050 (6)*
H4B	0.0829 (9)	0.485 (3)	0.3435 (14)	0.052 (6)*
H4A	0.1238 (8)	0.454 (3)	0.4042 (13)	0.043 (6)*
H2B	0.1917 (9)	0.666 (3)	0.4725 (14)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0446 (13)	0.0681 (13)	0.0736 (17)	−0.0058 (11)	0.0174 (12)	0.0051 (12)
C2	0.0501 (17)	0.107 (2)	0.115 (3)	−0.0029 (15)	0.0356 (18)	0.005 (2)
C3	0.077 (2)	0.125 (3)	0.135 (3)	0.0032 (19)	0.069 (2)	−0.012 (2)
C4	0.096 (2)	0.102 (2)	0.085 (2)	0.0014 (18)	0.0552 (19)	−0.0172 (17)
C5	0.0688 (15)	0.0494 (11)	0.0581 (14)	0.0021 (10)	0.0271 (12)	−0.0041 (10)
C6	0.0784 (18)	0.0595 (12)	0.0405 (12)	−0.0028 (12)	0.0168 (12)	−0.0056 (10)
C7	0.0616 (15)	0.0523 (11)	0.0414 (12)	0.0008 (10)	0.0017 (10)	0.0058 (9)
C8	0.0499 (12)	0.0523 (11)	0.0573 (14)	−0.0113 (10)	0.0150 (10)	−0.0018 (10)
C9	0.0566 (14)	0.0622 (13)	0.086 (2)	−0.0107 (11)	0.0271 (14)	0.0122 (13)
C10	0.0680 (16)	0.0727 (15)	0.0763 (18)	0.0119 (13)	0.0403 (14)	0.0257 (14)
C11	0.0643 (15)	0.0691 (14)	0.0469 (13)	0.0177 (12)	0.0221 (11)	0.0091 (11)
C12	0.0422 (11)	0.0507 (10)	0.0412 (10)	0.0092 (8)	0.0109 (9)	0.0028 (9)
C13	0.0606 (14)	0.0580 (12)	0.0442 (12)	−0.0021 (10)	0.0148 (10)	−0.0159 (10)
C14	0.0523 (12)	0.0358 (9)	0.0623 (14)	0.0000 (8)	0.0152 (10)	−0.0090 (9)
C15	0.0335 (10)	0.0379 (9)	0.0354 (10)	−0.0017 (7)	0.0048 (8)	−0.0008 (7)
C16	0.0482 (12)	0.0399 (9)	0.0420 (11)	−0.0030 (8)	−0.0004 (9)	0.0023 (8)
C17	0.0379 (10)	0.0355 (8)	0.0371 (10)	0.0011 (7)	0.0046 (9)	0.0034 (7)
C18	0.0391 (10)	0.0341 (8)	0.0368 (9)	0.0013 (7)	0.0036 (8)	0.0045 (7)
N1	0.0442 (10)	0.0479 (9)	0.0529 (10)	−0.0028 (7)	0.0181 (8)	−0.0007 (8)
N2	0.0373 (9)	0.0374 (8)	0.0429 (9)	0.0007 (7)	0.0023 (7)	−0.0019 (7)
N3	0.0379 (9)	0.0415 (8)	0.0390 (9)	−0.0037 (6)	0.0085 (7)	0.0004 (7)
N4	0.0386 (10)	0.0356 (8)	0.0447 (10)	−0.0031 (7)	0.0033 (8)	−0.0010 (7)
O1	0.0379 (7)	0.0416 (7)	0.0484 (8)	0.0058 (6)	−0.0039 (6)	−0.0029 (6)
O2	0.0651 (11)	0.0435 (7)	0.0744 (12)	−0.0173 (7)	−0.0155 (9)	0.0054 (7)
O3	0.0471 (8)	0.0340 (6)	0.0627 (10)	0.0011 (6)	0.0083 (7)	−0.0049 (6)
O4	0.0369 (7)	0.0426 (7)	0.0590 (9)	0.0006 (6)	0.0061 (7)	0.0018 (6)
O5	0.0455 (8)	0.0366 (7)	0.0543 (9)	0.0007 (6)	−0.0032 (7)	−0.0056 (7)
O6	0.081 (8)	0.056 (6)	0.196 (16)	0.000	−0.027 (9)	0.000
Ni1	0.03027 (13)	0.03237 (12)	0.03530 (13)	−0.00067 (9)	0.00469 (9)	−0.00121 (9)

C1—N1	1.344 (3)	C13—C14	1.527 (3)
C1—C2	1.371 (4)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.361 (5)	C14—N4	1.466 (3)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.371 (5)	C14—H14B	0.9700
C3—H3	0.9300	C15—O1	1.256 (2)
C4—C5	1.391 (4)	C15—C15i	1.442 (4)
C4—H4	0.9300	C15—C16	1.456 (3)
C5—N1	1.344 (3)	C16—O2	1.243 (2)
C5—C6	1.496 (4)	C16—C16i	1.464 (4)
C6—C7	1.516 (3)	C17—O3	1.250 (2)
C6—H6A	0.9700	C17—C18	1.465 (2)
C6—H6B	0.9700	C17—C18ii	1.465 (3)
C7—N2	1.471 (3)	C18—O4	1.251 (2)
C7—H7A	0.9700	C18—C17ii	1.465 (3)
C7—H7B	0.9700	N1—Ni1	2.1624 (17)
C8—N3	1.336 (3)	N2—Ni1	2.0576 (17)
C8—C9	1.374 (3)	N2—H2A	0.90 (2)
C8—H8	0.9300	N2—H2B	0.83 (2)
C9—C10	1.367 (4)	N3—Ni1	2.1495 (16)
C9—H9	0.9300	N4—Ni1	2.0833 (15)
C10—C11	1.372 (4)	N4—H4B	0.88 (2)
C10—H10	0.9300	N4—H4A	0.86 (2)
C11—C12	1.383 (3)	O1—Ni1	2.0803 (13)
C11—H11	0.9300	O5—Ni1	2.1126 (14)
C12—N3	1.344 (3)	O5—H5A	0.81 (3)
C12—C13	1.497 (3)	O5—H5B	0.81 (3)
N1—C1—C2	123.7 (3)	C13—C14—H14B	109.4
N1—C1—H1	118.2	H14A—C14—H14B	108.0
C2—C1—H1	118.2	O1—C15—C15i	132.78 (10)
C3—C2—C1	118.8 (3)	O1—C15—C16	136.79 (18)
C3—C2—H2	120.6	C15i—C15—C16	90.42 (11)
C1—C2—H2	120.6	O2—C16—C15	135.5 (2)
C2—C3—C4	118.5 (3)	O2—C16—C16i	134.90 (12)
C2—C3—H3	120.8	C15—C16—C16i	89.58 (11)
C4—C3—H3	120.8	O3—C17—C18	134.03 (18)
C3—C4—C5	120.7 (3)	O3—C17—C18ii	135.44 (18)
C3—C4—H4	119.6	C18—C17—C18ii	90.52 (15)
C5—C4—H4	119.6	O4—C18—C17ii	135.81 (17)
N1—C5—C4	120.4 (3)	O4—C18—C17	134.71 (17)
N1—C5—C6	118.8 (2)	C17ii—C18—C17	89.48 (15)
C4—C5—C6	120.8 (3)	C1—N1—C5	117.8 (2)
C5—C6—C7	115.41 (19)	C1—N1—Ni1	118.46 (16)
C5—C6—H6A	108.4	C5—N1—Ni1	122.50 (15)
C7—C6—H6A	108.4	C7—N2—Ni1	116.32 (14)
C5—C6—H6B	108.4	C7—N2—H2A	106.6 (15)
C7—C6—H6B	108.4	Ni1—N2—H2A	110.4 (14)
H6A—C6—H6B	107.5	C7—N2—H2B	109.6 (17)
N2—C7—C6	110.98 (18)	Ni1—N2—H2B	107.7 (17)
N2—C7—H7A	109.4	H2A—N2—H2B	106 (2)
C6—C7—H7A	109.4	C8—N3—C12	117.74 (18)
N2—C7—H7B	109.4	C8—N3—Ni1	118.55 (14)
C6—C7—H7B	109.4	C12—N3—Ni1	122.65 (13)
H7A—C7—H7B	108.0	C14—N4—Ni1	116.85 (12)
N3—C8—C9	123.5 (2)	C14—N4—H4B	108.3 (15)
N3—C8—H8	118.3	Ni1—N4—H4B	106.0 (14)
C9—C8—H8	118.3	C14—N4—H4A	108.5 (14)
C10—C9—C8	119.0 (2)	Ni1—N4—H4A	109.3 (14)
C10—C9—H9	120.5	H4B—N4—H4A	108 (2)
C8—C9—H9	120.5	C15—O1—Ni1	134.29 (12)
C9—C10—C11	118.2 (2)	Ni1—O5—H5A	131.0 (18)
C9—C10—H10	120.9	Ni1—O5—H5B	113.3 (18)
C11—C10—H10	120.9	H5A—O5—H5B	108 (3)
C10—C11—C12	120.5 (2)	N2—Ni1—O1	179.19 (7)
C10—C11—H11	119.8	N2—Ni1—N4	92.52 (7)
C12—C11—H11	119.8	O1—Ni1—N4	87.01 (6)
N3—C12—C11	121.1 (2)	N2—Ni1—O5	90.91 (7)
N3—C12—C13	118.03 (18)	O1—Ni1—O5	89.58 (6)
C11—C12—C13	120.9 (2)	N4—Ni1—O5	176.22 (7)
C12—C13—C14	113.80 (18)	N2—Ni1—N3	92.36 (7)
C12—C13—H13A	108.8	O1—Ni1—N3	86.99 (6)
C14—C13—H13A	108.8	N4—Ni1—N3	90.91 (7)
C12—C13—H13B	108.8	O5—Ni1—N3	90.53 (6)
C14—C13—H13B	108.8	N2—Ni1—N1	92.52 (7)
H13A—C13—H13B	107.7	O1—Ni1—N1	88.16 (7)
N4—C14—C13	111.35 (17)	N4—Ni1—N1	92.23 (7)
N4—C14—H14A	109.4	O5—Ni1—N1	86.03 (6)
C13—C14—H14A	109.4	N3—Ni1—N1	174.08 (6)
N4—C14—H14B	109.4
N1—C1—C2—C3	−1.4 (5)	C13—C12—N3—C8	174.5 (2)
C1—C2—C3—C4	−0.5 (5)	C11—C12—N3—Ni1	164.32 (16)
C2—C3—C4—C5	1.9 (5)	C13—C12—N3—Ni1	−17.4 (3)
C3—C4—C5—N1	−1.5 (4)	C13—C14—N4—Ni1	−48.4 (2)
C3—C4—C5—C6	179.7 (3)	C15i—C15—O1—Ni1	−148.2 (2)
N1—C5—C6—C7	−40.5 (3)	C16—C15—O1—Ni1	33.2 (4)
C4—C5—C6—C7	138.4 (2)	C7—N2—Ni1—N4	−85.75 (15)
C5—C6—C7—N2	79.8 (3)	C7—N2—Ni1—O5	92.66 (15)
N3—C8—C9—C10	0.4 (4)	C7—N2—Ni1—N3	−176.77 (14)
C8—C9—C10—C11	−1.3 (4)	C7—N2—Ni1—N1	6.59 (15)
C9—C10—C11—C12	−0.3 (4)	C15—O1—Ni1—N4	168.45 (19)
C10—C11—C12—N3	2.9 (3)	C15—O1—Ni1—O5	−9.92 (19)
C10—C11—C12—C13	−175.3 (2)	C15—O1—Ni1—N3	−100.47 (19)
N3—C12—C13—C14	−42.1 (3)	C15—O1—Ni1—N1	76.12 (19)
C11—C12—C13—C14	136.1 (2)	C14—N4—Ni1—N2	−92.56 (16)
C12—C13—C14—N4	80.6 (2)	C14—N4—Ni1—O1	86.78 (16)
O1—C15—C16—O2	−2.4 (5)	C14—N4—Ni1—N3	−0.16 (16)
C15i—C15—C16—O2	178.7 (3)	C14—N4—Ni1—N1	174.82 (16)
O1—C15—C16—C16i	178.5 (2)	C8—N3—Ni1—N2	−64.13 (16)
C15i—C15—C16—C16i	−0.4 (2)	C12—N3—Ni1—N2	127.95 (16)
O3—C17—C18—O4	0.7 (4)	C8—N3—Ni1—O1	116.36 (16)
C18ii—C17—C18—O4	−179.9 (3)	C12—N3—Ni1—O1	−51.57 (15)
O3—C17—C18—C17ii	−179.4 (3)	C8—N3—Ni1—N4	−156.69 (16)
C18ii—C17—C18—C17ii	0.0	C12—N3—Ni1—N4	35.39 (16)
C2—C1—N1—C5	1.8 (4)	C8—N3—Ni1—O5	26.81 (16)
C2—C1—N1—Ni1	−165.8 (2)	C12—N3—Ni1—O5	−141.12 (16)
C4—C5—N1—C1	−0.4 (3)	C1—N1—Ni1—N2	−164.45 (17)
C6—C5—N1—C1	178.5 (2)	C5—N1—Ni1—N2	28.56 (17)
C4—C5—N1—Ni1	166.70 (19)	C1—N1—Ni1—O1	15.11 (16)
C6—C5—N1—Ni1	−14.4 (3)	C5—N1—Ni1—O1	−151.88 (17)
C6—C7—N2—Ni1	−52.9 (2)	C1—N1—Ni1—N4	−71.83 (17)
C9—C8—N3—C12	2.1 (3)	C5—N1—Ni1—N4	121.19 (17)
C9—C8—N3—Ni1	−166.43 (19)	C1—N1—Ni1—O5	104.81 (17)
C11—C12—N3—C8	−3.7 (3)	C5—N1—Ni1—O5	−62.18 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4iii	0.81 (3)	1.93 (3)	2.716 (2)	163 (3)
N2—H2A···O3iii	0.90 (2)	2.09 (2)	2.935 (2)	157 (2)
O5—H5B···O2	0.81 (3)	1.87 (3)	2.675 (2)	172 (3)
N4—H4B···O2iv	0.88 (2)	2.52 (2)	3.078 (2)	122.6 (18)
N4—H4B···O6	0.88 (2)	2.52 (3)	3.350 (2)	158 (2)
N4—H4A···O4v	0.86 (2)	2.27 (2)	3.091 (2)	161 (2)
N2—H2B···O3vi	0.83 (2)	2.14 (3)	2.963 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4i	0.81 (3)	1.93 (3)	2.716 (2)	163 (3)
N2—H2A⋯O3i	0.90 (2)	2.09 (2)	2.935 (2)	157 (2)
O5—H5B⋯O2	0.81 (3)	1.87 (3)	2.675 (2)	172 (3)
N4—H4B⋯O2ii	0.88 (2)	2.52 (2)	3.078 (2)	122.6 (18)
N4—H4B⋯O6	0.88 (2)	2.52 (3)	3.350 (2)	158 (2)
N4—H4A⋯O4iii	0.86 (2)	2.27 (2)	3.091 (2)	161 (2)
N2—H2B⋯O3iv	0.83 (2)	2.14 (3)	2.963 (2)	169 (2)

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