Bis(μ-5-carboxyl-ato-1-carboxyl-ato-methyl-2-oxidopyridinium)-κO:O;κO:O-[diaqua-(phenan-throline-κN,N')manganese(II)] dihydrate.

The centrosymmetric binuclear title complex, [Mn(2)(C(8)H(5)NO(5))(2)(C(12)H(8)N(2))(2)(H(2)O)(4)]·2H(2)O, was obtained by the reaction of manganese chloride with 5-carb-oxy-1-carboxy-methyl-2-oxidopyridinium and 1,10-phenanthroline. The Mn(II) atom is coordinated by two N atoms from the 1,10-phenanthroline ligand, two O atoms from two 5-carboxyl-ato-1-carboxyl-atomethyl-2-oxidopyridinium ligands and two water mol-ecules, leading to a distorted octahedral MnN(2)O(4) environment. Inter-molecular O-H⋯O hydrogen bonds link neighbouring mol-ecules into a layer structure parallel to (001).

Related literature

For the synthesis of compounds with multicarboxyl­ate ligands and metal centers, see: He et al. (2008 ▶); Huang et al. (2008 ▶); Jiang et al. (2009 ▶); Tong et al. (2005 ▶).

Experimental

Crystal data

[Mn2(C8H5NO5)2(C12H8N2)2(H2O)4]·2H2O

M = 968.64

Triclinic,

a = 7.7726 (11) Å

b = 9.9519 (14) Å

c = 15.411 (3) Å

α = 98.744 (10)°

β = 103.553 (10)°

γ = 110.252 (7)°

V = 1051.1 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.68 mm−1

T = 293 K

0.60 × 0.15 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.934

19359 measured reflections

4779 independent reflections

3675 reflections with I > 2σ(I)

R int = 0.171

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.141

S = 1.00

4779 reflections

307 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.79 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809017668/at2783sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017668/at2783Isup2.hkl

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

[Mn2(C8H5NO5)2(C12H8N2)2(H2O)4]·2H2O	V = 1051.1 (3) Å3
Mr = 968.64	Z = 1
Triclinic, P1	F(000) = 498
Hall symbol: -P 1	Dx = 1.530 Mg m−3
a = 7.7726 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9519 (14) Å	θ = 2.8–27.5°
c = 15.411 (3) Å	µ = 0.68 mm−1
α = 98.744 (10)°	T = 293 K
β = 103.553 (10)°	Block, yellow
γ = 110.252 (7)°	0.60 × 0.15 × 0.10 mm

Bruker APEXII area-detector diffractometer	4779 independent reflections
Radiation source: fine-focus sealed tube	3675 reflections with I > 2σ(I)
graphite	Rint = 0.171
ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.885, Tmax = 0.934	k = −12→12
19359 measured reflections	l = −19→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.083P)2 + 0.0025P] where P = (Fo2 + 2Fc2)/3
4779 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.81 e Å−3
9 restraints	Δρmin = −0.79 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
Mn1	0.34180 (4)	0.38197 (3)	0.24659 (2)	0.03192 (14)
C1	0.8430 (3)	0.9583 (2)	0.60141 (17)	0.0399 (5)
H1A	0.7365	0.9575	0.5533	0.048*
H1B	0.9335	1.0605	0.6284	0.048*
C2	0.7670 (3)	0.89610 (18)	0.67529 (14)	0.0334 (4)
C3	1.1327 (3)	0.9121 (2)	0.60386 (16)	0.0416 (5)
C4	1.2123 (3)	0.8185 (2)	0.56435 (17)	0.0447 (5)
H4	1.3421	0.8388	0.5905	0.054*
C5	1.1068 (3)	0.7009 (2)	0.49014 (16)	0.0397 (5)
H5	1.1640	0.6423	0.4663	0.048*
C6	0.9079 (3)	0.66801 (19)	0.44911 (15)	0.0350 (5)
C7	0.8321 (3)	0.75625 (19)	0.48720 (15)	0.0358 (5)
H7	0.7016	0.7344	0.4620	0.043*
C8	0.7808 (3)	0.5421 (2)	0.36561 (15)	0.0363 (5)
C9	−0.0500 (3)	0.1365 (2)	0.09487 (19)	0.0561 (7)
H9	−0.0641	0.0926	0.1433	0.067*
C10	−0.1881 (4)	0.0671 (3)	0.0077 (2)	0.0672 (9)
H10	−0.2900	−0.0226	−0.0012	0.081*
C11	−0.1736 (3)	0.1298 (2)	−0.06335 (19)	0.0565 (7)
H11	−0.2654	0.0839	−0.1212	0.068*
C12	−0.0184 (3)	0.2654 (2)	−0.04935 (16)	0.0413 (5)
C13	0.0048 (3)	0.3422 (3)	−0.11964 (18)	0.0506 (6)
H13	−0.0821	0.2997	−0.1789	0.061*
C14	0.1498 (3)	0.4747 (3)	−0.10162 (17)	0.0495 (6)
H14	0.1607	0.5238	−0.1481	0.059*
C15	0.2884 (3)	0.5414 (2)	−0.01126 (16)	0.0405 (5)
C16	0.4418 (4)	0.6812 (2)	0.01077 (19)	0.0509 (6)
H16	0.4584	0.7336	−0.0338	0.061*
C17	0.5659 (3)	0.7382 (2)	0.09913 (19)	0.0509 (6)
H17	0.6660	0.8312	0.1156	0.061*
C18	0.5416 (3)	0.6564 (2)	0.16410 (17)	0.0429 (5)
H18	0.6289	0.6962	0.2234	0.051*
C19	0.2732 (3)	0.46827 (18)	0.05867 (14)	0.0331 (4)
C20	0.1150 (3)	0.32712 (18)	0.04029 (14)	0.0338 (4)
O1W	0.2082 (2)	0.51934 (15)	0.30069 (13)	0.0469 (4)
H1WA	0.107 (3)	0.494 (3)	0.3146 (19)	0.056*
H1WB	0.262 (3)	0.6101 (18)	0.3185 (18)	0.056*
O1	0.6879 (2)	0.96382 (15)	0.71523 (12)	0.0473 (4)
O2W	0.5101 (2)	0.24567 (16)	0.20164 (12)	0.0439 (4)
H2WA	0.612 (3)	0.297 (2)	0.2403 (16)	0.053*
H2WB	0.459 (3)	0.177 (2)	0.2261 (16)	0.053*
O2	0.7879 (2)	0.78107 (15)	0.68951 (12)	0.0440 (4)
O3	1.2212 (2)	1.02222 (18)	0.67190 (14)	0.0640 (6)
O3W	0.5827 (3)	1.18225 (16)	0.65623 (18)	0.0688 (6)
H3WA	0.632 (4)	1.129 (3)	0.680 (2)	0.083*
H3WB	0.471 (3)	1.149 (3)	0.659 (2)	0.083*
O4	0.84928 (19)	0.46805 (15)	0.32338 (12)	0.0449 (4)
O5	0.6043 (2)	0.52140 (18)	0.34392 (12)	0.0526 (5)
N1	0.9381 (2)	0.87521 (16)	0.56051 (13)	0.0361 (4)
N2	0.3998 (2)	0.52424 (16)	0.14566 (13)	0.0351 (4)
N3	0.0999 (2)	0.26257 (16)	0.11052 (13)	0.0390 (4)

	U11	U22	U33	U12	U13	U23
Mn1	0.03112 (19)	0.02749 (17)	0.0329 (2)	0.00883 (12)	0.00698 (15)	0.00713 (12)
C1	0.0513 (11)	0.0308 (8)	0.0417 (13)	0.0170 (8)	0.0180 (10)	0.0135 (8)
C2	0.0322 (9)	0.0295 (8)	0.0345 (12)	0.0102 (7)	0.0072 (8)	0.0069 (7)
C3	0.0390 (10)	0.0365 (9)	0.0403 (13)	0.0071 (8)	0.0112 (9)	0.0057 (8)
C4	0.0306 (9)	0.0466 (10)	0.0455 (14)	0.0107 (8)	0.0024 (9)	0.0055 (9)
C5	0.0340 (9)	0.0377 (9)	0.0433 (13)	0.0132 (8)	0.0079 (9)	0.0079 (8)
C6	0.0318 (9)	0.0330 (8)	0.0348 (12)	0.0092 (7)	0.0055 (8)	0.0098 (8)
C7	0.0331 (9)	0.0334 (8)	0.0360 (12)	0.0088 (7)	0.0066 (8)	0.0118 (8)
C8	0.0336 (9)	0.0343 (8)	0.0361 (12)	0.0094 (7)	0.0079 (8)	0.0094 (8)
C9	0.0537 (13)	0.0374 (10)	0.0535 (17)	−0.0012 (9)	0.0010 (12)	0.0158 (10)
C10	0.0565 (14)	0.0399 (11)	0.066 (2)	−0.0090 (10)	−0.0065 (13)	0.0106 (12)
C11	0.0491 (12)	0.0441 (11)	0.0491 (17)	0.0073 (9)	−0.0067 (11)	−0.0029 (10)
C12	0.0399 (10)	0.0406 (9)	0.0383 (13)	0.0177 (8)	0.0041 (9)	0.0038 (8)
C13	0.0523 (12)	0.0593 (13)	0.0370 (14)	0.0270 (11)	0.0037 (10)	0.0076 (10)
C14	0.0587 (13)	0.0624 (13)	0.0383 (14)	0.0315 (11)	0.0165 (11)	0.0235 (11)
C15	0.0467 (11)	0.0407 (9)	0.0425 (13)	0.0223 (9)	0.0184 (10)	0.0151 (9)
C16	0.0622 (14)	0.0437 (11)	0.0559 (16)	0.0202 (10)	0.0270 (12)	0.0265 (10)
C17	0.0540 (13)	0.0328 (9)	0.0608 (18)	0.0071 (9)	0.0225 (12)	0.0149 (10)
C18	0.0422 (10)	0.0306 (8)	0.0455 (15)	0.0061 (8)	0.0113 (10)	0.0039 (8)
C19	0.0364 (9)	0.0291 (8)	0.0360 (12)	0.0156 (7)	0.0120 (8)	0.0068 (7)
C20	0.0350 (9)	0.0301 (8)	0.0347 (12)	0.0144 (7)	0.0076 (8)	0.0050 (7)
O1W	0.0401 (8)	0.0323 (6)	0.0712 (13)	0.0146 (6)	0.0243 (8)	0.0096 (7)
O1	0.0589 (9)	0.0417 (7)	0.0532 (11)	0.0275 (7)	0.0266 (8)	0.0131 (7)
O2W	0.0446 (8)	0.0401 (7)	0.0439 (11)	0.0140 (6)	0.0143 (7)	0.0084 (7)
O2	0.0562 (9)	0.0403 (7)	0.0529 (11)	0.0258 (6)	0.0295 (8)	0.0251 (7)
O3	0.0481 (9)	0.0496 (9)	0.0649 (14)	0.0037 (7)	0.0082 (8)	−0.0152 (8)
O3W	0.0591 (10)	0.0344 (7)	0.1180 (19)	0.0198 (7)	0.0337 (12)	0.0212 (9)
O4	0.0352 (7)	0.0413 (7)	0.0505 (11)	0.0110 (6)	0.0120 (7)	0.0020 (7)
O5	0.0323 (7)	0.0601 (9)	0.0504 (11)	0.0180 (7)	0.0006 (7)	−0.0080 (8)
N1	0.0384 (8)	0.0304 (7)	0.0386 (11)	0.0108 (6)	0.0135 (7)	0.0104 (7)
N2	0.0344 (8)	0.0282 (7)	0.0383 (11)	0.0085 (6)	0.0113 (7)	0.0058 (6)
N3	0.0376 (8)	0.0286 (7)	0.0411 (11)	0.0059 (6)	0.0063 (8)	0.0085 (7)

Mn1—O5	2.0761 (14)	C10—C11	1.348 (4)
Mn1—O2i	2.1066 (15)	C10—H10	0.9300
Mn1—O1W	2.1643 (15)	C11—C12	1.409 (3)
Mn1—N2	2.2768 (18)	C11—H11	0.9300
Mn1—N3	2.2788 (17)	C12—C20	1.411 (3)
Mn1—O2W	2.3237 (17)	C12—C13	1.428 (3)
C1—N1	1.454 (3)	C13—C14	1.341 (3)
C1—C2	1.518 (3)	C13—H13	0.9300
C1—H1A	0.9700	C14—C15	1.436 (3)
C1—H1B	0.9700	C14—H14	0.9300
C2—O1	1.245 (2)	C15—C19	1.394 (3)
C2—O2	1.254 (2)	C15—C16	1.411 (3)
C3—O3	1.251 (2)	C16—C17	1.370 (4)
C3—N1	1.391 (3)	C16—H16	0.9300
C3—C4	1.423 (3)	C17—C18	1.390 (3)
C4—C5	1.356 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—N2	1.327 (2)
C5—C6	1.423 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—N2	1.361 (3)
C6—C7	1.352 (3)	C19—C20	1.444 (2)
C6—C8	1.503 (3)	C20—N3	1.348 (3)
C7—N1	1.356 (2)	O1W—H1WA	0.831 (16)
C7—H7	0.9300	O1W—H1WB	0.822 (15)
C8—O4	1.240 (3)	O2W—H2WA	0.807 (16)
C8—O5	1.267 (2)	O2W—H2WB	0.856 (16)
C9—N3	1.324 (2)	O2—Mn1i	2.1066 (15)
C9—C10	1.401 (3)	O3W—H3WA	0.833 (17)
C9—H9	0.9300	O3W—H3WB	0.833 (17)
O5—Mn1—O2i	105.32 (7)	C10—C11—C12	119.5 (2)
O5—Mn1—O1W	89.47 (6)	C10—C11—H11	120.2
O2i—Mn1—O1W	90.24 (6)	C12—C11—H11	120.2
O5—Mn1—N2	90.90 (7)	C11—C12—C20	116.6 (2)
O2i—Mn1—N2	163.71 (6)	C11—C12—C13	123.4 (2)
O1W—Mn1—N2	88.34 (7)	C20—C12—C13	120.00 (19)
O5—Mn1—N3	162.47 (8)	C14—C13—C12	121.1 (2)
O2i—Mn1—N3	91.35 (6)	C14—C13—H13	119.5
O1W—Mn1—N3	95.98 (7)	C12—C13—H13	119.5
N2—Mn1—N3	72.68 (6)	C13—C14—C15	120.6 (2)
O5—Mn1—O2W	85.20 (6)	C13—C14—H14	119.7
O2i—Mn1—O2W	89.67 (6)	C15—C14—H14	119.7
O1W—Mn1—O2W	174.44 (6)	C19—C15—C16	117.6 (2)
N2—Mn1—O2W	93.29 (6)	C19—C15—C14	120.02 (19)
N3—Mn1—O2W	89.58 (6)	C16—C15—C14	122.4 (2)
N1—C1—C2	112.73 (16)	C17—C16—C15	118.7 (2)
N1—C1—H1A	109.0	C17—C16—H16	120.7
C2—C1—H1A	109.0	C15—C16—H16	120.7
N1—C1—H1B	109.0	C16—C17—C18	119.7 (2)
C2—C1—H1B	109.0	C16—C17—H17	120.1
H1A—C1—H1B	107.8	C18—C17—H17	120.1
O1—C2—O2	126.3 (2)	N2—C18—C17	123.2 (2)
O1—C2—C1	116.48 (17)	N2—C18—H18	118.4
O2—C2—C1	117.18 (19)	C17—C18—H18	118.4
O3—C3—N1	118.6 (2)	N2—C19—C15	123.24 (17)
O3—C3—C4	126.2 (2)	N2—C19—C20	117.09 (18)
N1—C3—C4	115.20 (17)	C15—C19—C20	119.66 (18)
C5—C4—C3	122.79 (19)	N3—C20—C12	123.26 (18)
C5—C4—H4	118.6	N3—C20—C19	118.13 (17)
C3—C4—H4	118.6	C12—C20—C19	118.59 (19)
C4—C5—C6	119.4 (2)	Mn1—O1W—H1WA	128.8 (17)
C4—C5—H5	120.3	Mn1—O1W—H1WB	122.9 (17)
C6—C5—H5	120.3	H1WA—O1W—H1WB	108 (2)
C7—C6—C5	117.71 (18)	Mn1—O2W—H2WA	96 (2)
C7—C6—C8	119.05 (17)	Mn1—O2W—H2WB	93.0 (18)
C5—C6—C8	123.23 (19)	H2WA—O2W—H2WB	104 (2)
C6—C7—N1	122.87 (18)	C2—O2—Mn1i	134.18 (16)
C6—C7—H7	118.6	H3WA—O3W—H3WB	104 (2)
N1—C7—H7	118.6	C8—O5—Mn1	140.26 (15)
O4—C8—O5	124.86 (19)	C7—N1—C3	121.96 (18)
O4—C8—C6	120.83 (18)	C7—N1—C1	119.42 (17)
O5—C8—C6	114.31 (19)	C3—N1—C1	118.32 (17)
N3—C9—C10	122.1 (2)	C18—N2—C19	117.50 (19)
N3—C9—H9	118.9	C18—N2—Mn1	126.40 (15)
C10—C9—H9	118.9	C19—N2—Mn1	116.08 (12)
C11—C10—C9	120.2 (2)	C9—N3—C20	118.22 (18)
C11—C10—H10	119.9	C9—N3—Mn1	125.89 (16)
C9—C10—H10	119.9	C20—N3—Mn1	115.89 (12)
N1—C1—C2—O1	178.22 (17)	N2—Mn1—O5—C8	−84.9 (3)
N1—C1—C2—O2	−2.5 (3)	N3—Mn1—O5—C8	−64.8 (4)
O3—C3—C4—C5	−179.9 (3)	O2W—Mn1—O5—C8	8.3 (3)
N1—C3—C4—C5	−0.4 (3)	C6—C7—N1—C3	−2.2 (3)
C3—C4—C5—C6	0.0 (4)	C6—C7—N1—C1	−175.7 (2)
C4—C5—C6—C7	−0.6 (3)	O3—C3—N1—C7	−179.1 (2)
C4—C5—C6—C8	178.7 (2)	C4—C3—N1—C7	1.5 (3)
C5—C6—C7—N1	1.6 (3)	O3—C3—N1—C1	−5.4 (3)
C8—C6—C7—N1	−177.63 (18)	C4—C3—N1—C1	175.09 (19)
C7—C6—C8—O4	172.8 (2)	C2—C1—N1—C7	87.7 (2)
C5—C6—C8—O4	−6.4 (3)	C2—C1—N1—C3	−86.1 (2)
C7—C6—C8—O5	−6.9 (3)	C17—C18—N2—C19	−0.3 (3)
C5—C6—C8—O5	173.9 (2)	C17—C18—N2—Mn1	−178.77 (18)
N3—C9—C10—C11	−1.5 (5)	C15—C19—N2—C18	1.4 (3)
C9—C10—C11—C12	0.2 (5)	C20—C19—N2—C18	−177.59 (18)
C10—C11—C12—C20	0.3 (4)	C15—C19—N2—Mn1	−179.97 (16)
C10—C11—C12—C13	−177.8 (3)	C20—C19—N2—Mn1	1.1 (2)
C11—C12—C13—C14	176.6 (2)	O5—Mn1—N2—C18	−9.93 (18)
C20—C12—C13—C14	−1.5 (4)	O2i—Mn1—N2—C18	164.7 (2)
C12—C13—C14—C15	1.3 (4)	O1W—Mn1—N2—C18	79.51 (18)
C13—C14—C15—C19	0.2 (3)	N3—Mn1—N2—C18	176.30 (19)
C13—C14—C15—C16	−179.3 (2)	O2W—Mn1—N2—C18	−95.17 (18)
C19—C15—C16—C17	−0.7 (3)	O5—Mn1—N2—C19	171.54 (14)
C14—C15—C16—C17	178.9 (2)	O2i—Mn1—N2—C19	−13.9 (3)
C15—C16—C17—C18	1.7 (4)	O1W—Mn1—N2—C19	−99.02 (14)
C16—C17—C18—N2	−1.3 (4)	N3—Mn1—N2—C19	−2.23 (13)
C16—C15—C19—N2	−0.9 (3)	O2W—Mn1—N2—C19	86.30 (14)
C14—C15—C19—N2	179.6 (2)	C10—C9—N3—C20	2.0 (4)
C16—C15—C19—C20	178.02 (19)	C10—C9—N3—Mn1	−177.0 (2)
C14—C15—C19—C20	−1.5 (3)	C12—C20—N3—C9	−1.4 (3)
C11—C12—C20—N3	0.2 (3)	C19—C20—N3—C9	176.9 (2)
C13—C12—C20—N3	178.5 (2)	C12—C20—N3—Mn1	177.73 (16)
C11—C12—C20—C19	−178.11 (19)	C19—C20—N3—Mn1	−3.9 (2)
C13—C12—C20—C19	0.1 (3)	O5—Mn1—N3—C9	161.2 (2)
N2—C19—C20—N3	1.9 (3)	O2i—Mn1—N3—C9	−0.9 (2)
C15—C19—C20—N3	−177.08 (18)	O1W—Mn1—N3—C9	−91.3 (2)
N2—C19—C20—C12	−179.65 (18)	N2—Mn1—N3—C9	−177.7 (2)
C15—C19—C20—C12	1.4 (3)	O2W—Mn1—N3—C9	88.7 (2)
O1—C2—O2—Mn1i	17.7 (3)	O5—Mn1—N3—C20	−17.9 (3)
C1—C2—O2—Mn1i	−161.47 (15)	O2i—Mn1—N3—C20	179.98 (15)
O4—C8—O5—Mn1	1.0 (4)	O1W—Mn1—N3—C20	89.60 (15)
C6—C8—O5—Mn1	−179.30 (18)	N2—Mn1—N3—C20	3.23 (14)
O2i—Mn1—O5—C8	96.6 (3)	O2W—Mn1—N3—C20	−90.35 (15)
O1W—Mn1—O5—C8	−173.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ii	0.83 (2)	1.97 (2)	2.773 (2)	163 (3)
O1W—H1WB···O3Wiii	0.82 (2)	1.92 (2)	2.730 (2)	169 (3)
O2W—H2WA···O4	0.81 (2)	2.00 (2)	2.783 (2)	164 (2)
O2W—H2WA···O5	0.81 (2)	2.57 (3)	2.984 (2)	114 (2)
O2W—H2WB···O1i	0.86 (2)	1.96 (2)	2.806 (2)	170 (3)
O3W—H3WA···O1	0.83 (2)	1.96 (2)	2.775 (2)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4i	0.831 (16)	1.967 (18)	2.773 (2)	163 (3)
O1W—H1WB⋯O3Wii	0.822 (15)	1.920 (15)	2.730 (2)	169 (3)
O2W—H2WA⋯O4	0.807 (16)	1.998 (15)	2.783 (2)	164 (2)
O2W—H2WA⋯O5	0.807 (16)	2.57 (3)	2.984 (2)	114 (2)
O2W—H2WB⋯O1iii	0.856 (16)	1.959 (16)	2.806 (2)	170 (3)
O3W—H3WA⋯O1	0.833 (17)	1.962 (19)	2.775 (2)	165 (3)

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