Diaqua-bis-{4-[(pyridin-2-yl)methyl-idene-amino]-benzene-sulfonato-κ(2)N,N'}nickel(II) tetra-hydrate.

In the title complex, [Ni(C(12)H(9)N(2)O(3)S)(2)(H(2)O)(2)]·4H(2)O, the Ni(II) ion is coordinated by four N atoms from two bidentate chelating 4-[(pyridin-2-yl)methyl-idene-amino]-benzene-sulfonate ligands and two O atoms from cis-related water mol-ecules in a slightly distorted octa-hedral environment [Ni-N = 2.071 (3)-2.121 (3) Å and Ni-O = 2.071 (2) and 2.073 (3) Å]. In the crystal, the coordinated water mol-ecules and the four water mol-ecules of solvation are involved in inter-molecular O-H⋯O hydrogen-bonding inter-actions with water and sulfon-ate O-atom acceptors, giving a three-dimensional framework structure.

Related literature

For the synthesis of the ligand, see: Casella & Gullotti (1981 ▶). For the synthesis, structures and applications of similar complexes, see: Zhang et al. (2007 ▶, 2008 ▶). For the structures of the mainly tridentate complexes with the title ligand and similar ligands, see: Correia et al. (2003 ▶); Jiang et al. (2006 ▶); Ou-Yang et al. (2008 ▶); Li et al. (2006 ▶); Huang et al. (2009 ▶).

Experimental

Crystal data

[Ni(C12H9N2O3S)2(H2O)2]·4H2O

M = 689.35

Orthorhombic,

a = 13.865 (2) Å

b = 11.5310 (18) Å

c = 18.860 (3) Å

V = 3015.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.85 mm−1

T = 296 K

0.36 × 0.19 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.821, T max = 0.889

16541 measured reflections

5315 independent reflections

4983 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.100

S = 0.96

5315 reflections

388 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 2540 Friedel pairs

Flack parameter: 0.00 (1)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022179/zs2208sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022179/zs2208Isup2.hkl

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

[Ni(C12H9N2O3S)2(H2O)2]·4H2O	F(000) = 1432
Mr = 689.35	Dx = 1.518 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5315 reflections
a = 13.865 (2) Å	θ = 2.1–25.1°
b = 11.5310 (18) Å	µ = 0.85 mm−1
c = 18.860 (3) Å	T = 296 K
V = 3015.3 (8) Å3	Prism, blue
Z = 4	0.36 × 0.19 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	5315 independent reflections
Radiation source: fine-focus sealed tube	4983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→15
Tmin = 0.821, Tmax = 0.889	k = −12→13
16541 measured reflections	l = −21→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0792P)2 + 0.0306P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
5315 reflections	Δρmax = 0.44 e Å−3
388 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 2540 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (1)

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
Ni1	0.20498 (2)	1.02094 (3)	0.40723 (2)	0.02752 (11)
S1	0.73596 (6)	1.04204 (7)	0.44399 (5)	0.03481 (19)
S2	−0.05169 (7)	0.72312 (8)	0.70323 (5)	0.0424 (2)
C1	0.1419 (2)	0.8284 (3)	0.51959 (18)	0.0344 (7)
C2	0.0425 (3)	0.8359 (3)	0.51285 (19)	0.0416 (8)
H2	0.0154	0.8610	0.4704	0.050*
C3	−0.0162 (3)	0.8060 (3)	0.5690 (2)	0.0433 (8)
H3	−0.0829	0.8099	0.5643	0.052*
C4	0.0244 (3)	0.7701 (3)	0.63258 (18)	0.0367 (7)
C5	0.1233 (3)	0.7666 (4)	0.64016 (19)	0.0446 (9)
H5	0.1505	0.7449	0.6832	0.053*
C6	0.1825 (3)	0.7957 (4)	0.5830 (2)	0.0439 (9)
H6	0.2492	0.7930	0.5879	0.053*
C7	0.2621 (3)	0.7887 (3)	0.4372 (2)	0.0383 (7)
H7	0.2700	0.7168	0.4588	0.046*
C8	0.3219 (2)	0.8221 (3)	0.37556 (19)	0.0345 (7)
C9	0.3888 (3)	0.7478 (4)	0.3452 (2)	0.0517 (9)
H9	0.3983	0.6740	0.3637	0.062*
C10	0.4408 (3)	0.7847 (4)	0.2875 (2)	0.0613 (12)
H10	0.4874	0.7369	0.2673	0.074*
C11	0.4233 (3)	0.8925 (4)	0.2600 (2)	0.0554 (11)
H11	0.4573	0.9190	0.2207	0.067*
C12	0.3539 (3)	0.9611 (3)	0.2919 (2)	0.0407 (8)
H12	0.3417	1.0342	0.2730	0.049*
C13	0.4683 (2)	1.0089 (3)	0.52834 (19)	0.0393 (8)
H13	0.4397	0.9777	0.5687	0.047*
C14	0.5673 (3)	1.0014 (3)	0.5188 (2)	0.0399 (8)
H14	0.6053	0.9657	0.5530	0.048*
C15	0.6096 (2)	1.0470 (3)	0.45836 (18)	0.0335 (7)
C16	0.5529 (2)	1.0996 (3)	0.4065 (2)	0.0369 (7)
H16	0.5814	1.1292	0.3657	0.044*
C17	0.4550 (2)	1.1077 (3)	0.41573 (19)	0.0356 (7)
H17	0.4171	1.1426	0.3811	0.043*
C18	0.4121 (2)	1.0635 (3)	0.47707 (18)	0.0316 (6)
C19	0.2719 (2)	1.1073 (3)	0.54054 (19)	0.0383 (8)
H19	0.3101	1.1220	0.5801	0.046*
C20	0.1660 (2)	1.1226 (3)	0.5437 (2)	0.0390 (8)
C21	0.1207 (3)	1.1581 (6)	0.6040 (3)	0.0727 (16)
H21	0.1552	1.1711	0.6455	0.087*
C22	0.0210 (3)	1.1745 (6)	0.6016 (3)	0.0765 (16)
H22	−0.0121	1.1990	0.6418	0.092*
C23	−0.0268 (3)	1.1544 (4)	0.5405 (2)	0.0517 (10)
H23	−0.0932	1.1646	0.5382	0.062*
C24	0.0239 (2)	1.1186 (3)	0.4818 (2)	0.0399 (8)
H24	−0.0093	1.1060	0.4397	0.048*
N1	0.20060 (18)	0.8593 (2)	0.45990 (15)	0.0318 (6)
N2	0.30403 (16)	0.9275 (2)	0.34813 (15)	0.0292 (6)
N3	0.30951 (17)	1.0737 (2)	0.48275 (15)	0.0297 (6)
N4	0.11907 (18)	1.1011 (2)	0.48314 (14)	0.0318 (6)
O1	0.22444 (18)	1.1677 (2)	0.34556 (13)	0.0394 (5)
H1A	0.2096	1.1876	0.3036	0.059*
H1	0.2364	1.2285	0.3694	0.059*
O2	0.09435 (18)	0.9625 (2)	0.34255 (14)	0.0463 (6)
H2B	0.0449	1.0005	0.3295	0.069*
H2A	0.1204	0.9324	0.3061	0.069*
O3	0.77809 (19)	0.9764 (2)	0.50163 (16)	0.0438 (6)
O4	0.76778 (18)	1.1617 (2)	0.44222 (19)	0.0562 (7)
O5	0.7506 (2)	0.9857 (3)	0.37643 (17)	0.0624 (8)
O6	0.0109 (2)	0.7141 (3)	0.76410 (16)	0.0728 (9)
O7	−0.1269 (2)	0.8077 (3)	0.71181 (17)	0.0644 (8)
O8	−0.0890 (3)	0.6119 (3)	0.68130 (19)	0.0814 (12)
O1W	0.1482 (2)	0.8187 (3)	0.23302 (17)	0.0613 (8)
H1WA	0.1788	0.7548	0.2339	0.092*
H1WB	0.1766	0.8647	0.2047	0.092*
O2W	0.2203 (3)	−0.0066 (3)	0.1507 (2)	0.0764 (10)
H2WA	0.2499	0.0164	0.1126	0.115*
H2WB	0.1642	0.0260	0.1517	0.115*
O4W	0.1939 (3)	0.5819 (3)	0.2341 (2)	0.0784 (10)
H4WB	0.1951	0.5164	0.2134	0.118*
H4WA	0.2094	0.5718	0.2775	0.118*
O3W	0.9288 (2)	0.0644 (4)	0.3082 (2)	0.0940 (13)
H3WB	0.9386	0.1276	0.2860	0.141*
H3WA	0.8695	0.0599	0.3187	0.141*

	U11	U22	U33	U12	U13	U23
Ni1	0.02597 (19)	0.0301 (2)	0.0265 (2)	0.00072 (14)	0.00129 (17)	0.00007 (19)
S1	0.0260 (4)	0.0403 (4)	0.0381 (4)	0.0023 (3)	−0.0034 (4)	0.0044 (4)
S2	0.0496 (5)	0.0457 (5)	0.0319 (4)	−0.0013 (4)	0.0112 (4)	0.0058 (4)
C1	0.0388 (17)	0.0286 (16)	0.0359 (18)	−0.0041 (13)	0.0049 (14)	0.0026 (13)
C2	0.0422 (18)	0.053 (2)	0.0296 (18)	−0.0063 (16)	−0.0020 (14)	0.0095 (15)
C3	0.0361 (17)	0.057 (2)	0.0371 (19)	−0.0087 (16)	0.0010 (15)	0.0071 (16)
C4	0.0438 (18)	0.0354 (17)	0.0308 (17)	−0.0037 (15)	0.0077 (14)	0.0043 (13)
C5	0.044 (2)	0.056 (2)	0.0336 (19)	0.0032 (17)	−0.0003 (15)	0.0141 (16)
C6	0.0357 (17)	0.055 (2)	0.041 (2)	0.0057 (16)	0.0024 (15)	0.0056 (17)
C7	0.0445 (17)	0.0305 (16)	0.0398 (18)	0.0017 (14)	0.0043 (15)	0.0059 (15)
C8	0.0350 (16)	0.0336 (18)	0.0348 (16)	0.0045 (14)	0.0023 (14)	−0.0009 (14)
C9	0.051 (2)	0.050 (2)	0.054 (2)	0.0147 (18)	0.0089 (18)	0.0039 (19)
C10	0.057 (2)	0.070 (3)	0.057 (3)	0.026 (2)	0.021 (2)	0.000 (2)
C11	0.047 (2)	0.076 (3)	0.043 (2)	0.002 (2)	0.0176 (17)	0.003 (2)
C12	0.0419 (19)	0.042 (2)	0.038 (2)	−0.0046 (15)	0.0028 (15)	0.0034 (15)
C13	0.0344 (19)	0.048 (2)	0.0360 (19)	0.0017 (14)	0.0031 (15)	0.0152 (15)
C14	0.0326 (18)	0.051 (2)	0.036 (2)	0.0058 (15)	−0.0025 (15)	0.0153 (15)
C15	0.0310 (16)	0.0329 (16)	0.0366 (19)	−0.0008 (13)	−0.0035 (13)	0.0025 (14)
C16	0.0287 (14)	0.0475 (18)	0.0345 (16)	−0.0057 (12)	−0.0021 (15)	0.0108 (17)
C17	0.0296 (14)	0.0442 (18)	0.0330 (17)	−0.0031 (12)	−0.0049 (14)	0.0097 (15)
C18	0.0263 (14)	0.0344 (16)	0.0340 (17)	−0.0036 (13)	−0.0017 (13)	0.0031 (13)
C19	0.0304 (16)	0.056 (2)	0.0288 (18)	−0.0049 (15)	−0.0009 (13)	−0.0048 (15)
C20	0.0333 (17)	0.048 (2)	0.0353 (18)	−0.0010 (15)	−0.0001 (14)	−0.0068 (15)
C21	0.038 (2)	0.137 (5)	0.043 (2)	0.002 (2)	0.0019 (18)	−0.031 (3)
C22	0.041 (2)	0.130 (5)	0.059 (3)	0.001 (3)	0.014 (2)	−0.039 (3)
C23	0.0325 (18)	0.068 (3)	0.055 (2)	0.0020 (16)	0.0051 (17)	−0.014 (2)
C24	0.0313 (16)	0.0436 (18)	0.045 (2)	0.0031 (14)	−0.0040 (15)	−0.0055 (15)
N1	0.0340 (14)	0.0281 (13)	0.0332 (15)	−0.0024 (10)	0.0056 (10)	0.0037 (11)
N2	0.0262 (12)	0.0304 (15)	0.0309 (15)	−0.0020 (10)	0.0041 (10)	−0.0031 (11)
N3	0.0272 (12)	0.0332 (14)	0.0287 (14)	−0.0021 (10)	−0.0006 (11)	0.0004 (11)
N4	0.0301 (13)	0.0322 (14)	0.0331 (15)	0.0001 (10)	0.0037 (11)	−0.0023 (11)
O1	0.0539 (13)	0.0300 (12)	0.0342 (13)	0.0023 (10)	−0.0040 (11)	0.0049 (10)
O2	0.0380 (13)	0.0588 (16)	0.0421 (15)	0.0019 (11)	−0.0068 (11)	−0.0094 (12)
O3	0.0369 (13)	0.0453 (15)	0.0491 (17)	0.0051 (10)	−0.0089 (11)	0.0065 (12)
O4	0.0345 (12)	0.0447 (15)	0.089 (2)	−0.0049 (11)	−0.0096 (14)	0.0229 (16)
O5	0.0443 (17)	0.097 (2)	0.0458 (17)	0.0119 (15)	0.0030 (14)	−0.0110 (17)
O6	0.075 (2)	0.107 (3)	0.0359 (16)	−0.002 (2)	0.0060 (14)	0.0233 (17)
O7	0.0660 (18)	0.077 (2)	0.0499 (18)	0.0180 (15)	0.0253 (15)	0.0135 (16)
O8	0.110 (3)	0.061 (2)	0.073 (2)	−0.0346 (18)	0.047 (2)	−0.0115 (16)
O1W	0.0578 (17)	0.0614 (18)	0.065 (2)	−0.0034 (14)	0.0028 (14)	−0.0054 (15)
O2W	0.096 (3)	0.081 (2)	0.052 (2)	0.0126 (19)	0.0092 (17)	0.0085 (18)
O4W	0.100 (3)	0.062 (2)	0.073 (2)	−0.0125 (18)	−0.0150 (19)	0.0097 (18)
O3W	0.0498 (19)	0.129 (3)	0.103 (3)	0.015 (2)	0.0142 (19)	0.046 (3)

Ni1—N2	2.071 (3)	C12—H12	0.9300
Ni1—O1	2.071 (2)	C13—C14	1.387 (5)
Ni1—O2	2.073 (3)	C13—C18	1.392 (5)
Ni1—N4	2.079 (3)	C13—H13	0.9300
Ni1—N1	2.113 (3)	C14—C15	1.385 (5)
Ni1—N3	2.121 (3)	C14—H14	0.9300
S1—O5	1.444 (3)	C15—C16	1.393 (5)
S1—O3	1.448 (3)	C16—C17	1.371 (4)
S1—O4	1.449 (3)	C16—H16	0.9300
S1—C15	1.774 (3)	C17—C18	1.397 (5)
S2—O7	1.437 (3)	C17—H17	0.9300
S2—O8	1.443 (3)	C18—N3	1.431 (4)
S2—O6	1.443 (3)	C19—N3	1.269 (5)
S2—C4	1.784 (3)	C19—C20	1.480 (5)
C1—C6	1.375 (5)	C19—H19	0.9300
C1—C2	1.387 (5)	C20—N4	1.338 (5)
C1—N1	1.434 (4)	C20—C21	1.362 (6)
C2—C3	1.380 (5)	C21—C22	1.396 (6)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.387 (5)	C22—C23	1.349 (6)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.379 (5)	C23—C24	1.375 (5)
C5—C6	1.395 (5)	C23—H23	0.9300
C5—H5	0.9300	C24—N4	1.335 (4)
C6—H6	0.9300	C24—H24	0.9300
C7—N1	1.254 (4)	O1—H1A	0.8499
C7—C8	1.479 (5)	O1—H1	0.8500
C7—H7	0.9300	O2—H2B	0.8500
C8—N2	1.344 (4)	O2—H2A	0.8500
C8—C9	1.386 (5)	O1W—H1WA	0.8506
C9—C10	1.374 (6)	O1W—H1WB	0.8501
C9—H9	0.9300	O2W—H2WA	0.8684
C10—C11	1.369 (6)	O2W—H2WB	0.8637
C10—H10	0.9300	O4W—H4WB	0.8501
C11—C12	1.384 (6)	O4W—H4WA	0.8538
C11—H11	0.9300	O3W—H3WB	0.8511
C12—N2	1.324 (4)	O3W—H3WA	0.8476
N2—Ni1—O1	92.09 (10)	N2—C12—H12	118.5
N2—Ni1—O2	90.27 (10)	C11—C12—H12	118.5
O1—Ni1—O2	91.81 (10)	C14—C13—C18	119.4 (3)
N2—Ni1—N4	169.04 (11)	C14—C13—H13	120.3
O1—Ni1—N4	95.63 (10)	C18—C13—H13	120.3
O2—Ni1—N4	97.23 (11)	C15—C14—C13	120.1 (3)
N2—Ni1—N1	79.24 (11)	C15—C14—H14	119.9
O1—Ni1—N1	171.32 (10)	C13—C14—H14	119.9
O2—Ni1—N1	88.20 (10)	C14—C15—C16	120.2 (3)
N4—Ni1—N1	92.98 (11)	C14—C15—S1	122.1 (3)
N2—Ni1—N3	93.30 (10)	C16—C15—S1	117.6 (3)
O1—Ni1—N3	93.09 (10)	C17—C16—C15	119.9 (3)
O2—Ni1—N3	173.83 (11)	C17—C16—H16	120.0
N4—Ni1—N3	78.55 (10)	C15—C16—H16	120.0
N1—Ni1—N3	87.53 (11)	C16—C17—C18	120.1 (3)
O5—S1—O3	111.75 (17)	C16—C17—H17	120.0
O5—S1—O4	111.4 (2)	C18—C17—H17	120.0
O3—S1—O4	113.12 (18)	C13—C18—C17	120.1 (3)
O5—S1—C15	106.73 (18)	C13—C18—N3	122.8 (3)
O3—S1—C15	107.49 (16)	C17—C18—N3	117.1 (3)
O4—S1—C15	105.88 (15)	N3—C19—C20	118.6 (3)
O7—S2—O8	112.0 (2)	N3—C19—H19	120.7
O7—S2—O6	113.3 (2)	C20—C19—H19	120.7
O8—S2—O6	112.3 (2)	N4—C20—C21	123.0 (3)
O7—S2—C4	107.90 (17)	N4—C20—C19	115.2 (3)
O8—S2—C4	105.55 (18)	C21—C20—C19	121.8 (3)
O6—S2—C4	105.09 (17)	C20—C21—C22	118.1 (4)
C6—C1—C2	120.2 (3)	C20—C21—H21	120.9
C6—C1—N1	121.3 (3)	C22—C21—H21	120.9
C2—C1—N1	118.5 (3)	C23—C22—C21	119.3 (4)
C3—C2—C1	120.0 (3)	C23—C22—H22	120.3
C3—C2—H2	120.0	C21—C22—H22	120.3
C1—C2—H2	120.0	C22—C23—C24	119.2 (3)
C2—C3—C4	119.9 (3)	C22—C23—H23	120.4
C2—C3—H3	120.1	C24—C23—H23	120.4
C4—C3—H3	120.1	N4—C24—C23	122.3 (3)
C5—C4—C3	120.2 (3)	N4—C24—H24	118.8
C5—C4—S2	120.1 (3)	C23—C24—H24	118.8
C3—C4—S2	119.7 (3)	C7—N1—C1	119.5 (3)
C4—C5—C6	119.8 (3)	C7—N1—Ni1	113.1 (2)
C4—C5—H5	120.1	C1—N1—Ni1	127.2 (2)
C6—C5—H5	120.1	C12—N2—C8	118.5 (3)
C1—C6—C5	119.8 (3)	C12—N2—Ni1	128.7 (2)
C1—C6—H6	120.1	C8—N2—Ni1	112.7 (2)
C5—C6—H6	120.1	C19—N3—C18	119.9 (3)
N1—C7—C8	118.7 (3)	C19—N3—Ni1	112.6 (2)
N1—C7—H7	120.7	C18—N3—Ni1	127.2 (2)
C8—C7—H7	120.7	C20—N4—C24	118.0 (3)
N2—C8—C9	121.5 (3)	C20—N4—Ni1	113.0 (2)
N2—C8—C7	115.8 (3)	C24—N4—Ni1	128.3 (2)
C9—C8—C7	122.6 (3)	Ni1—O1—H1A	135.5
C10—C9—C8	119.2 (4)	Ni1—O1—H1	113.7
C10—C9—H9	120.4	H1A—O1—H1	108.5
C8—C9—H9	120.4	Ni1—O2—H2B	126.8
C9—C10—C11	119.2 (4)	Ni1—O2—H2A	107.1
C9—C10—H10	120.4	H2B—O2—H2A	108.6
C11—C10—H10	120.4	H1WA—O1W—H1WB	108.8
C10—C11—C12	118.6 (4)	H2WA—O2W—H2WB	108.2
C10—C11—H11	120.7	H4WB—O4W—H4WA	108.3
C12—C11—H11	120.7	H3WB—O3W—H3WA	108.7
N2—C12—C11	123.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.85	1.92	2.748 (4)	166
O1—H1A···O7ii	0.85	2.08	2.876 (4)	156
O2—H2A···O1W	0.85	1.94	2.752 (4)	159
O2—H2B···O3Wiii	0.85	1.82	2.659 (4)	171
O1W—H1WA···O4W	0.85	2.00	2.804 (5)	156
O1W—H1WB···O2Wiv	0.85	1.90	2.733 (5)	167
O2W—H2WA···O3v	0.87	2.13	2.833 (5)	137
O2W—H2WB···O7vi	0.86	2.29	2.874 (5)	125
O3W—H3WB···O6v	0.85	2.00	2.813 (6)	160
O3W—H3WA···O5vii	0.85	2.15	2.930 (5)	152
O4W—H4WB···O8vi	0.85	2.17	2.846 (5)	136
O4W—H4WA···O5viii	0.85	2.06	2.903 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.85	1.92	2.748 (4)	166
O1—H1A⋯O7ii	0.85	2.08	2.876 (4)	156
O2—H2A⋯O1W	0.85	1.94	2.752 (4)	159
O2—H2B⋯O3Wiii	0.85	1.82	2.659 (4)	171
O1W—H1WA⋯O4W	0.85	2.00	2.804 (5)	156
O1W—H1WB⋯O2Wiv	0.85	1.90	2.733 (5)	167
O2W—H2WA⋯O3v	0.87	2.13	2.833 (5)	137
O2W—H2WB⋯O7vi	0.86	2.29	2.874 (5)	125
O3W—H3WB⋯O6v	0.85	2.00	2.813 (6)	160
O3W—H3WA⋯O5vii	0.85	2.15	2.930 (5)	152
O4W—H4WB⋯O8vi	0.85	2.17	2.846 (5)	136
O4W—H4WA⋯O5viii	0.85	2.06	2.903 (5)	169

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