Penta-aqua-(5-carb-oxy-pyridine-2-carboxyl-ato-κN,O)(pyridine-2,5-dicarboxyl-ato-κN,O)cerium(III) tetra-hydrate.

In the title compound, [Ce(C(7)H(3)NO(4))(C(7)H(4)NO(4))(H(2)O)(5)]·4H(2)O, the Ce(3+) ion is nine-coordinated by two O atoms and two N atoms from one single and from one double deprotonated pyridine-2,5-dicarboxyl-ate ligand and five water mol-ecules in a distorted monocapped square-anti-prismatic geometry. In the crystal, extensive O-H⋯O hydrogen-bonding inter-actions result in a three-dimensional supra-molecular architecture.

Related literature

For luminescent lanthanide complexes, see: Faulkner & Pope (2003 ▶). For carb­oxy­lic complexes of lanthanides, see: Cao et al. (2002 ▶). For a related europium structure, see: Song et al. (2005 ▶).

Experimental

Crystal data

[Ce(C7H3NO4)(C7H4NO4)(H2O)5]·4H2O

M = 633.48

Monoclinic,

a = 14.0652 (10) Å

b = 9.6485 (7) Å

c = 33.345 (2) Å

β = 93.650 (1)°

V = 4516.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 2.10 mm−1

T = 296 K

0.36 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.518, T max = 0.716

11155 measured reflections

3961 independent reflections

3705 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.050

S = 1.07

3961 reflections

383 parameters

28 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052688/ez2275sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052688/ez2275Isup2.hkl

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

[Ce(C7H3NO4)(C7H4NO4)(H2O)5]·4H2O	F(000) = 2536
Mr = 633.48	Dx = 1.863 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2168 reflections
a = 14.0652 (10) Å	θ = 2.6–22.7°
b = 9.6485 (7) Å	µ = 2.10 mm−1
c = 33.345 (2) Å	T = 296 K
β = 93.650 (1)°	Block, colorless
V = 4516.0 (6) Å3	0.36 × 0.24 × 0.17 mm
Z = 8

Bruker SMART APEX CCD diffractometer	3961 independent reflections
Radiation source: fine-focus sealed tube	3705 reflections with I > 2σ(I)
graphite	Rint = 0.019
phi and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→12
Tmin = 0.518, Tmax = 0.716	k = −11→11
11155 measured reflections	l = −38→39

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0224P)2 + 6.9052P] where P = (Fo2 + 2Fc2)/3
3961 reflections	(Δ/σ)max = 0.002
383 parameters	Δρmax = 0.45 e Å−3
28 restraints	Δρmin = −0.50 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
Ce1	0.894634 (10)	−0.318396 (14)	0.381434 (4)	0.01818 (6)
O1	0.97858 (13)	−0.54167 (19)	0.38596 (5)	0.0277 (4)
O2	1.07372 (15)	−0.70191 (18)	0.41446 (6)	0.0304 (4)
O3	1.10159 (16)	−0.0673 (2)	0.53150 (6)	0.0372 (5)
O4	1.17536 (16)	−0.2284 (2)	0.56975 (6)	0.0370 (5)
O5	0.88653 (14)	−0.15016 (18)	0.32391 (5)	0.0285 (4)
O6	0.87079 (16)	−0.08997 (19)	0.25957 (5)	0.0357 (5)
O7	0.88037 (18)	−0.8380 (2)	0.27999 (6)	0.0374 (5)
O8	0.85018 (17)	−0.79869 (19)	0.21507 (6)	0.0385 (5)
N1	1.02240 (15)	−0.3588 (2)	0.44467 (6)	0.0211 (5)
N2	0.87500 (15)	−0.4203 (2)	0.30610 (6)	0.0212 (5)
C1	1.04597 (19)	−0.2665 (3)	0.47348 (8)	0.0235 (6)
H1A	1.0159	−0.1805	0.4724	0.028*
C2	1.11345 (19)	−0.2927 (3)	0.50507 (8)	0.0229 (6)
C3	1.1603 (2)	−0.4173 (3)	0.50519 (8)	0.0295 (6)
H3A	1.2068	−0.4375	0.5254	0.035*
C4	1.1381 (2)	−0.5126 (3)	0.47515 (8)	0.0300 (6)
H4A	1.1702	−0.5968	0.4746	0.036*
C5	1.06761 (18)	−0.4811 (3)	0.44591 (7)	0.0202 (5)
C6	1.1322 (2)	−0.1883 (3)	0.53826 (8)	0.0253 (6)
C7	1.03803 (18)	−0.5827 (3)	0.41309 (7)	0.0219 (6)
C8	0.87469 (19)	−0.3296 (3)	0.27554 (8)	0.0209 (5)
C9	0.8724 (2)	−0.3706 (3)	0.23619 (8)	0.0307 (7)
H9A	0.8722	−0.3052	0.2157	0.037*
C10	0.8705 (2)	−0.5100 (3)	0.22733 (8)	0.0316 (7)
H10A	0.8691	−0.5399	0.2008	0.038*
C11	0.87054 (19)	−0.6052 (3)	0.25841 (8)	0.0231 (6)
C12	0.87281 (18)	−0.5545 (3)	0.29736 (7)	0.0228 (6)
H12A	0.8728	−0.6177	0.3184	0.027*
C13	0.87783 (19)	−0.1775 (3)	0.28743 (8)	0.0222 (6)
C14	0.86649 (19)	−0.7566 (3)	0.24921 (8)	0.0237 (6)
O1W	0.92616 (16)	−0.0802 (2)	0.40398 (6)	0.0348 (5)
H1WA	0.939 (2)	−0.024 (2)	0.3864 (6)	0.039 (10)*
H1WB	0.911 (2)	−0.037 (3)	0.4241 (6)	0.049 (10)*
O2W	0.81108 (15)	−0.2775 (2)	0.44579 (6)	0.0351 (5)
H2WA	0.7607 (14)	−0.313 (3)	0.4527 (9)	0.048 (11)*
H2WB	0.837 (2)	−0.235 (4)	0.4650 (8)	0.074 (14)*
O3W	0.78056 (16)	−0.5204 (2)	0.38981 (7)	0.0369 (5)
H3WA	0.7345 (15)	−0.528 (3)	0.3730 (7)	0.041 (10)*
H3WB	0.796 (2)	−0.5992 (18)	0.3977 (10)	0.060 (12)*
O4W	1.05648 (15)	−0.2898 (2)	0.35667 (7)	0.0334 (5)
H4WA	1.076 (2)	−0.2140 (18)	0.3486 (10)	0.042 (10)*
H4WB	1.1030 (15)	−0.339 (3)	0.3637 (11)	0.052 (11)*
O5W	0.72275 (14)	−0.2396 (2)	0.36277 (6)	0.0329 (5)
H5WA	0.6985 (19)	−0.254 (4)	0.3399 (4)	0.044 (10)*
H5WB	0.6823 (18)	−0.240 (4)	0.3798 (7)	0.056 (12)*
O6W	0.64591 (16)	−0.3678 (3)	0.47916 (7)	0.0428 (5)
H6WA	0.611 (2)	−0.333 (3)	0.4610 (9)	0.065 (13)*
H6WB	0.626 (3)	−0.444 (2)	0.4860 (13)	0.099 (18)*
O7W	0.62864 (17)	−0.5498 (2)	0.33125 (8)	0.0420 (5)
H7WA	0.5957 (19)	−0.486 (2)	0.3394 (8)	0.034 (10)*
H7WB	0.639 (3)	−0.539 (4)	0.3073 (5)	0.104 (19)*
O8W	0.99039 (18)	0.1264 (2)	0.35587 (7)	0.0412 (5)
H8WA	1.001 (3)	0.192 (2)	0.3712 (9)	0.061 (13)*
H8WB	0.948 (2)	0.143 (3)	0.3385 (8)	0.060 (13)*
O9W	1.22355 (19)	−0.4211 (3)	0.37170 (9)	0.0614 (8)
H9WA	1.253 (2)	−0.387 (3)	0.3916 (7)	0.057 (12)*
H9WB	1.242 (3)	−0.5001 (19)	0.3673 (11)	0.076 (15)*
H7	0.872 (3)	−0.9185 (19)	0.2726 (13)	0.092 (16)*

	U11	U22	U33	U12	U13	U23
Ce1	0.02396 (9)	0.01492 (9)	0.01536 (9)	0.00190 (6)	−0.00097 (6)	−0.00118 (6)
O1	0.0359 (11)	0.0211 (9)	0.0247 (10)	0.0035 (8)	−0.0088 (8)	−0.0039 (8)
O2	0.0415 (12)	0.0176 (10)	0.0313 (11)	0.0075 (8)	−0.0046 (9)	−0.0043 (8)
O3	0.0661 (15)	0.0216 (11)	0.0231 (10)	0.0080 (10)	−0.0039 (10)	−0.0027 (8)
O4	0.0574 (14)	0.0276 (11)	0.0237 (11)	0.0007 (10)	−0.0157 (10)	−0.0027 (9)
O5	0.0482 (12)	0.0171 (9)	0.0197 (10)	−0.0011 (8)	−0.0015 (9)	−0.0011 (8)
O6	0.0706 (15)	0.0152 (9)	0.0207 (10)	−0.0017 (9)	−0.0025 (10)	0.0026 (8)
O7	0.0731 (16)	0.0152 (10)	0.0222 (11)	−0.0016 (10)	−0.0101 (10)	−0.0005 (9)
O8	0.0713 (16)	0.0210 (11)	0.0220 (11)	0.0018 (10)	−0.0055 (10)	−0.0049 (8)
N1	0.0262 (12)	0.0199 (11)	0.0167 (11)	0.0053 (9)	−0.0028 (9)	−0.0024 (9)
N2	0.0299 (12)	0.0148 (11)	0.0186 (11)	0.0009 (9)	−0.0013 (9)	−0.0001 (9)
C1	0.0297 (15)	0.0191 (13)	0.0212 (13)	0.0062 (11)	−0.0021 (11)	−0.0022 (11)
C2	0.0283 (14)	0.0203 (13)	0.0202 (13)	−0.0014 (11)	0.0015 (11)	−0.0005 (11)
C3	0.0358 (16)	0.0270 (15)	0.0242 (14)	0.0074 (12)	−0.0102 (12)	−0.0016 (12)
C4	0.0383 (16)	0.0230 (15)	0.0276 (15)	0.0116 (12)	−0.0059 (12)	−0.0025 (12)
C5	0.0251 (13)	0.0184 (13)	0.0171 (13)	0.0015 (10)	0.0011 (10)	0.0012 (10)
C6	0.0333 (15)	0.0220 (14)	0.0205 (14)	−0.0038 (12)	0.0018 (12)	−0.0008 (11)
C7	0.0264 (14)	0.0200 (14)	0.0194 (13)	0.0008 (11)	0.0027 (11)	0.0010 (11)
C8	0.0256 (14)	0.0166 (13)	0.0205 (13)	0.0003 (10)	0.0002 (11)	0.0011 (10)
C9	0.0567 (19)	0.0186 (14)	0.0170 (14)	−0.0001 (13)	0.0035 (13)	0.0031 (11)
C10	0.0559 (19)	0.0238 (15)	0.0150 (13)	−0.0010 (13)	0.0005 (13)	−0.0034 (11)
C11	0.0299 (14)	0.0178 (13)	0.0215 (13)	0.0015 (11)	−0.0003 (11)	−0.0020 (11)
C12	0.0338 (15)	0.0164 (13)	0.0179 (13)	0.0007 (11)	−0.0006 (11)	0.0029 (10)
C13	0.0273 (14)	0.0163 (13)	0.0227 (14)	0.0012 (10)	0.0001 (11)	0.0001 (11)
C14	0.0291 (14)	0.0213 (14)	0.0203 (14)	0.0008 (11)	−0.0022 (11)	−0.0008 (11)
O1W	0.0619 (14)	0.0211 (10)	0.0218 (11)	−0.0011 (10)	0.0059 (10)	−0.0045 (9)
O2W	0.0323 (12)	0.0480 (14)	0.0254 (11)	−0.0050 (10)	0.0057 (9)	−0.0072 (10)
O3W	0.0375 (13)	0.0286 (12)	0.0431 (13)	−0.0053 (10)	−0.0086 (10)	0.0091 (10)
O4W	0.0310 (12)	0.0286 (12)	0.0412 (12)	0.0020 (10)	0.0078 (10)	0.0096 (10)
O5W	0.0303 (11)	0.0440 (13)	0.0238 (11)	0.0048 (10)	−0.0025 (9)	−0.0030 (10)
O6W	0.0406 (13)	0.0395 (14)	0.0476 (15)	0.0021 (11)	−0.0033 (11)	0.0162 (12)
O7W	0.0461 (14)	0.0355 (13)	0.0439 (14)	−0.0044 (11)	−0.0002 (11)	0.0143 (11)
O8W	0.0617 (16)	0.0291 (12)	0.0316 (12)	−0.0064 (11)	−0.0068 (11)	−0.0066 (10)
O9W	0.0550 (16)	0.0467 (16)	0.078 (2)	0.0185 (13)	−0.0337 (14)	−0.0271 (15)

Ce1—O1W	2.4493 (19)	C4—H4A	0.9300
Ce1—O1	2.4566 (18)	C5—C7	1.508 (4)
Ce1—O4W	2.486 (2)	C8—C9	1.369 (4)
Ce1—O5	2.5098 (18)	C8—C13	1.520 (3)
Ce1—O2W	2.542 (2)	C9—C10	1.377 (4)
Ce1—O3W	2.551 (2)	C9—H9A	0.9300
Ce1—O5W	2.573 (2)	C10—C11	1.384 (4)
Ce1—N2	2.695 (2)	C10—H10A	0.9300
Ce1—N1	2.710 (2)	C11—C12	1.386 (4)
O1—C7	1.256 (3)	C11—C14	1.493 (4)
O2—C7	1.254 (3)	C12—H12A	0.9300
O3—C6	1.259 (3)	O1W—H1WA	0.828 (10)
O4—C6	1.241 (3)	O1W—H1WB	0.830 (10)
O5—C13	1.243 (3)	O2W—H2WA	0.832 (10)
O6—C13	1.255 (3)	O2W—H2WB	0.829 (10)
O7—C14	1.297 (3)	O3W—H3WA	0.833 (10)
O7—H7	0.820 (10)	O3W—H3WB	0.831 (10)
O8—C14	1.217 (3)	O4W—H4WA	0.830 (10)
N1—C1	1.337 (3)	O4W—H4WB	0.828 (10)
N1—C5	1.340 (3)	O5W—H5WA	0.828 (10)
N2—C12	1.327 (3)	O5W—H5WB	0.829 (10)
N2—C8	1.343 (3)	O6W—H6WA	0.826 (10)
C1—C2	1.395 (4)	O6W—H6WB	0.827 (10)
C1—H1A	0.9300	O7W—H7WA	0.825 (10)
C2—C3	1.370 (4)	O7W—H7WB	0.826 (10)
C2—C6	1.508 (4)	O8W—H8WA	0.824 (10)
C3—C4	1.381 (4)	O8W—H8WB	0.825 (10)
C3—H3A	0.9300	O9W—H9WA	0.825 (10)
C4—C5	1.380 (4)	O9W—H9WB	0.821 (10)
O1W—Ce1—O1	136.63 (7)	C4—C3—H3A	120.1
O1W—Ce1—O4W	81.14 (7)	C5—C4—C3	119.0 (2)
O1—Ce1—O4W	70.80 (7)	C5—C4—H4A	120.5
O1W—Ce1—O5	68.06 (6)	C3—C4—H4A	120.5
O1—Ce1—O5	127.76 (6)	N1—C5—C4	122.3 (2)
O4W—Ce1—O5	70.87 (7)	N1—C5—C7	116.2 (2)
O1W—Ce1—O2W	71.32 (7)	C4—C5—C7	121.5 (2)
O1—Ce1—O2W	109.29 (7)	O4—C6—O3	125.8 (3)
O4W—Ce1—O2W	138.20 (7)	O4—C6—C2	117.7 (2)
O5—Ce1—O2W	122.95 (7)	O3—C6—C2	116.5 (2)
O1W—Ce1—O3W	141.81 (7)	O2—C7—O1	124.2 (2)
O1—Ce1—O3W	68.07 (7)	O2—C7—C5	118.6 (2)
O4W—Ce1—O3W	135.80 (7)	O1—C7—C5	117.2 (2)
O5—Ce1—O3W	125.42 (7)	N2—C8—C9	122.5 (2)
O2W—Ce1—O3W	72.45 (7)	N2—C8—C13	115.6 (2)
O1W—Ce1—O5W	86.90 (7)	C9—C8—C13	121.8 (2)
O1—Ce1—O5W	135.61 (7)	C8—C9—C10	119.1 (2)
O4W—Ce1—O5W	138.86 (7)	C8—C9—H9A	120.4
O5—Ce1—O5W	68.15 (7)	C10—C9—H9A	120.4
O2W—Ce1—O5W	71.37 (7)	C9—C10—C11	119.2 (2)
O3W—Ce1—O5W	70.39 (7)	C9—C10—H10A	120.4
O1W—Ce1—N2	129.35 (6)	C11—C10—H10A	120.4
O1—Ce1—N2	75.98 (6)	C10—C11—C12	117.8 (2)
O4W—Ce1—N2	76.86 (7)	C10—C11—C14	119.8 (2)
O5—Ce1—N2	61.75 (6)	C12—C11—C14	122.4 (2)
O2W—Ce1—N2	144.87 (7)	N2—C12—C11	123.3 (2)
O3W—Ce1—N2	78.20 (7)	N2—C12—H12A	118.4
O5W—Ce1—N2	80.99 (6)	C11—C12—H12A	118.4
O1W—Ce1—N1	78.35 (7)	O5—C13—O6	125.5 (2)
O1—Ce1—N1	62.21 (6)	O5—C13—C8	117.3 (2)
O4W—Ce1—N1	72.46 (7)	O6—C13—C8	117.2 (2)
O5—Ce1—N1	133.10 (7)	O8—C14—O7	123.3 (2)
O2W—Ce1—N1	71.63 (7)	O8—C14—C11	121.4 (2)
O3W—Ce1—N1	101.26 (7)	O7—C14—C11	115.3 (2)
O5W—Ce1—N1	142.85 (6)	Ce1—O1W—H1WA	116 (2)
N2—Ce1—N1	134.12 (6)	Ce1—O1W—H1WB	132 (2)
C7—O1—Ce1	128.03 (16)	H1WA—O1W—H1WB	108 (2)
C13—O5—Ce1	127.41 (16)	Ce1—O2W—H2WA	128 (2)
C14—O7—H7	109 (3)	Ce1—O2W—H2WB	122 (2)
C1—N1—C5	118.0 (2)	H2WA—O2W—H2WB	109 (2)
C1—N1—Ce1	125.81 (17)	Ce1—O3W—H3WA	117 (2)
C5—N1—Ce1	116.15 (16)	Ce1—O3W—H3WB	125 (2)
C12—N2—C8	118.1 (2)	H3WA—O3W—H3WB	109 (2)
C12—N2—Ce1	124.06 (16)	Ce1—O4W—H4WA	122 (2)
C8—N2—Ce1	117.68 (16)	Ce1—O4W—H4WB	124 (2)
N1—C1—C2	123.2 (2)	H4WA—O4W—H4WB	109 (2)
N1—C1—H1A	118.4	Ce1—O5W—H5WA	120 (2)
C2—C1—H1A	118.4	Ce1—O5W—H5WB	121 (2)
C3—C2—C1	117.7 (2)	H5WA—O5W—H5WB	112 (2)
C3—C2—C6	121.5 (2)	H6WA—O6W—H6WB	112 (2)
C1—C2—C6	120.8 (2)	H7WA—O7W—H7WB	111 (2)
C2—C3—C4	119.7 (3)	H8WA—O8W—H8WB	112 (2)
C2—C3—H3A	120.1	H9WA—O9W—H9WB	111 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O8W	0.83 (1)	1.94 (1)	2.747 (3)	165 (3)
O1W—H1WB···O3i	0.83 (1)	1.81 (1)	2.630 (3)	170 (3)
O2W—H2WA···O6W	0.83 (1)	1.96 (1)	2.779 (3)	167 (3)
O2W—H2WB···O6Wii	0.83 (1)	2.11 (2)	2.898 (3)	159 (3)
O3W—H3WA···O7W	0.83 (1)	1.98 (1)	2.816 (3)	177 (3)
O3W—H3WB···O4iii	0.83 (1)	2.01 (1)	2.823 (3)	165 (4)
O4W—H4WA···O7Wiv	0.83 (1)	1.86 (1)	2.687 (3)	175 (3)
O4W—H4WB···O9W	0.83 (1)	1.88 (1)	2.689 (3)	166 (3)
O5W—H5WA···O8v	0.83 (1)	1.96 (1)	2.789 (3)	175 (3)
O5W—H5WB···O2vi	0.83 (1)	2.01 (1)	2.821 (3)	167 (4)
O6W—H6WA···O2vi	0.83 (1)	2.04 (2)	2.823 (3)	157 (3)
O6W—H6WB···O3vii	0.83 (1)	1.97 (3)	2.698 (3)	146 (4)
O7W—H7WA···O8Wvii	0.83 (1)	1.94 (1)	2.747 (4)	164 (3)
O7W—H7WB···O6viii	0.83 (1)	2.28 (2)	3.054 (3)	157 (5)
O7W—H7WB···O8v	0.83 (1)	2.45 (4)	2.898 (3)	115 (3)
O8W—H8WA···O2ix	0.82 (1)	2.00 (2)	2.765 (3)	155 (3)
O8W—H8WA···O1ix	0.82 (1)	2.64 (2)	3.364 (3)	148 (3)
O8W—H8WB···O7ix	0.83 (1)	2.12 (2)	2.901 (3)	158 (4)
O9W—H9WA···O4x	0.83 (1)	1.94 (1)	2.750 (3)	167 (4)
O9W—H9WB···O5Wxi	0.82 (1)	2.33 (2)	3.087 (4)	154 (4)
O7—H7···O6xii	0.82 (1)	1.71 (1)	2.526 (3)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O8W	0.83 (1)	1.94 (1)	2.747 (3)	165 (3)
O1W—H1WB⋯O3i	0.83 (1)	1.81 (1)	2.630 (3)	170 (3)
O2W—H2WA⋯O6W	0.83 (1)	1.96 (1)	2.779 (3)	167 (3)
O2W—H2WB⋯O6Wii	0.83 (1)	2.11 (2)	2.898 (3)	159 (3)
O3W—H3WA⋯O7W	0.83 (1)	1.98 (1)	2.816 (3)	177 (3)
O3W—H3WB⋯O4iii	0.83 (1)	2.01 (1)	2.823 (3)	165 (4)
O4W—H4WA⋯O7Wiv	0.83 (1)	1.86 (1)	2.687 (3)	175 (3)
O4W—H4WB⋯O9W	0.83 (1)	1.88 (1)	2.689 (3)	166 (3)
O5W—H5WA⋯O8v	0.83 (1)	1.96 (1)	2.789 (3)	175 (3)
O5W—H5WB⋯O2vi	0.83 (1)	2.01 (1)	2.821 (3)	167 (4)
O6W—H6WA⋯O2vi	0.83 (1)	2.04 (2)	2.823 (3)	157 (3)
O6W—H6WB⋯O3vii	0.83 (1)	1.97 (3)	2.698 (3)	146 (4)
O7W—H7WA⋯O8Wvii	0.83 (1)	1.94 (1)	2.747 (4)	164 (3)
O7W—H7WB⋯O6viii	0.83 (1)	2.28 (2)	3.054 (3)	157 (5)
O7W—H7WB⋯O8v	0.83 (1)	2.45 (4)	2.898 (3)	115 (3)
O8W—H8WA⋯O2ix	0.82 (1)	2.00 (2)	2.765 (3)	155 (3)
O8W—H8WA⋯O1ix	0.82 (1)	2.64 (2)	3.364 (3)	148 (3)
O8W—H8WB⋯O7ix	0.83 (1)	2.12 (2)	2.901 (3)	158 (4)
O9W—H9WA⋯O4x	0.83 (1)	1.94 (1)	2.750 (3)	167 (4)
O9W—H9WB⋯O5Wxi	0.82 (1)	2.33 (2)	3.087 (4)	154 (4)
O7—H7⋯O6xii	0.82 (1)	1.71 (1)	2.526 (3)	173 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) ; (xi) ; (xii) .