Decaaqua­bis[μ₂-(5-carboxyl­ato-m-phenyl­enedi­oxy)diacetato]trizinc(II) dihydrate

In the crystal structure of the title compound, [Zn₃(C₁₁H₇O₈)₂(H₂O)₁₀]·2H₂O, the trianionic carboxyl­ate unit uses one oxyacetate –OCH₂CO₂⁻ arm to chelate a Zn atom through the ether and carboxylate O atoms. The other oxyacetate arm is free; the –CO₂⁻ end has a formal negative charge. The central Zn atom lies on a special position of site symmetry . The uncoordinated water mol­ecules form a three-dimensional hydrogen-bonded network. One solvent water molecule is disordered over two positions in a 2:1 ratio.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.027
• wR factor = 0.067
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H5W2   ..  H6W2    ..       2.08 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.742     0.878
            Tmin and Tmax expected:      0.659     0.875
            RR =      1.122
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.12
PLAT145_ALERT_4_C su on beta     Small or Missing  (x 10000) .....          1 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          5
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.46 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         13
PLAT736_ALERT_1_C H...A   Calc     1.93(3), Rep   1.930(10) ......       3.00 su-Ra
              H6#  -O2      1.555   1.465
PLAT736_ALERT_1_C H...A   Calc     1.91(3), Rep   1.910(10) ......       3.00 su-Ra
              H7#  -O4      1.555   2.667
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         18

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Related literature

The reaction of zinc cations and (5-carboxylato-m-phenylenedioxy)diacetate trianions in water gives crystalline hexaaquazinc bis[[(5-carboxylato-m-phenylenedioxy)diacetato]triaquazincate] heptahydrate, whose anion exists as a carboxylate-bridged chain (Wen & Ng, 2007).

S1. Experimental

(5-Carboxy-m-phenylenedioxy)diacetic acid (0.282 g, 1 mol) and zinc nitrate hexahydrate (0.298 g, 1 mmol)) were mixed in 20 ml e thanol-water (1:1, v/v) solution. The pH value was adjusted to 7 by sodium carbonate solution. The filtered solution was set aside for the growth of crystals which appeared after a week.

In an earlier attempt, the filtered solution was set aside for a week for the growth of hexaaquazinc bis[(5-carboxylato-m-phenylenedioxy)diacetatotriaquazincate] heptahydrate (Wen & Ng, 2007). In the present study, the solution was kept at 278 K for two months to yield a compound of a different composition.

S2. Refinement

The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.85 (1) Å and H···H 1.39 (1) Å); their temperature factors were freely refined. For the disordered lattce water molecule, hydrogen atoms were placed on the major component only. The carbon-bound H-atoms were generated geometrically (C–H 0.93 to 0.97 Å); they were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

Fig. 1. Thermal ellipsoid plot depicting the coordination geometries of the two zinc atoms; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. The minor disorder component of the lattice water molecule is not shown. [Symmery code (i) 2 – x, –y, 1 – z.]

Decaaquabis[µ₂-(5-carboxylato-m-phenylenedioxy)diacetato]trizinc(II) dihydrate

Crystal data

[Zn3(C11H7O8)2(H2O)10]·2H2O	Z = 1
Mr = 946.63	F(000) = 484
Triclinic, P1	Dx = 1.866 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3125 (1) Å	Cell parameters from 5082 reflections
b = 9.0935 (1) Å	θ = 2.6–27.2°
c = 13.4543 (2) Å	µ = 2.23 mm^−1
α = 79.271 (1)°	T = 295 K
β = 82.6340 (1)°	Prism, colorless
γ = 74.064 (1)°	0.32 × 0.16 × 0.06 mm
V = 842.42 (2) Å^3

Data collection

Bruker APEX-II area-detector diffractometer	3858 independent reflections
Radiation source: fine-focus sealed tube	3176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ϕ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.742, Tmax = 0.878	k = −11→11
14462 measured reflections	l = −16→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.2695P] where P = (Fo^2 + 2Fc^2)/3
3858 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.42 e Å^−3
18 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	1.0000	0.0000	0.5000	0.02497 (9)
Zn2	0.25698 (3)	0.73433 (3)	0.898344 (17)	0.02466 (8)
O1	0.9264 (2)	−0.15104 (16)	0.61275 (10)	0.0281 (3)
O2	0.7610 (2)	−0.19883 (17)	0.75921 (11)	0.0298 (3)
O3	0.7885 (2)	0.15379 (15)	0.60092 (10)	0.0262 (3)
O4	0.4623 (2)	0.54817 (17)	0.84086 (10)	0.0281 (3)
O5	0.3464 (2)	0.75350 (16)	0.73226 (11)	0.0281 (3)
O6	0.7776 (2)	0.65455 (16)	0.41363 (10)	0.0270 (3)
O7	0.8774 (3)	0.83786 (18)	0.25159 (12)	0.0449 (5)
O8	0.9369 (2)	0.65423 (17)	0.15490 (11)	0.0310 (4)
O1w	0.7706 (2)	−0.00283 (19)	0.42077 (12)	0.0326 (4)
H1w1	0.741 (4)	0.0793 (17)	0.3784 (17)	0.069 (10)*
H1w2	0.794 (5)	−0.0807 (19)	0.3909 (19)	0.080 (12)*
O2w	0.0493 (2)	0.94000 (19)	0.89410 (14)	0.0400 (4)
H2w1	0.066 (4)	1.016 (2)	0.8510 (17)	0.062 (9)*
H2w2	−0.061 (2)	0.957 (3)	0.922 (2)	0.083 (12)*
O3w	0.0360 (2)	0.63529 (19)	0.89035 (13)	0.0331 (4)
H3w1	0.059 (3)	0.5422 (12)	0.8821 (18)	0.044 (8)*
H3w2	−0.042 (4)	0.693 (2)	0.8485 (19)	0.070 (10)*
O4w	0.2654 (3)	0.6729 (2)	1.05019 (12)	0.0404 (4)
H4w1	0.355 (3)	0.603 (3)	1.079 (2)	0.073 (10)*
H4w2	0.1602 (19)	0.667 (3)	1.0834 (18)	0.054 (9)*
O5w	0.4649 (2)	0.8552 (2)	0.89952 (12)	0.0313 (4)
H5w1	0.550 (3)	0.847 (3)	0.8501 (12)	0.047 (8)*
H5w2	0.520 (4)	0.837 (4)	0.9540 (11)	0.090 (13)*
O6w	−0.2748 (4)	0.8784 (3)	1.0180 (2)	0.0378 (10)	0.671 (6)
H6w1	−0.223 (6)	0.793 (3)	1.054 (3)	0.126 (17)*
H6w2	−0.338 (7)	0.941 (4)	1.058 (3)	0.17 (2)*
O6w'	−0.4015 (10)	0.8303 (8)	1.0841 (6)	0.062 (3)	0.329 (6)
C1	0.8089 (3)	−0.1096 (2)	0.68481 (15)	0.0223 (4)
C2	0.7164 (3)	0.0612 (2)	0.68664 (16)	0.0297 (5)
H2A	0.5793	0.0811	0.6859	0.036*
H2B	0.7422	0.0892	0.7486	0.036*
C3	0.7317 (3)	0.3135 (2)	0.59859 (14)	0.0204 (4)
C4	0.6293 (3)	0.3834 (2)	0.67841 (15)	0.0220 (4)
H4	0.5972	0.3243	0.7389	0.026*
C5	0.5750 (3)	0.5446 (2)	0.66633 (15)	0.0205 (4)
C6	0.6244 (3)	0.6330 (2)	0.57711 (14)	0.0215 (4)
H6	0.5864	0.7405	0.5693	0.026*
C7	0.7317 (3)	0.5591 (2)	0.49913 (14)	0.0210 (4)
C8	0.7852 (3)	0.3998 (2)	0.50908 (15)	0.0219 (4)
H8	0.8562	0.3510	0.4564	0.026*
C9	0.4563 (3)	0.6204 (2)	0.75028 (14)	0.0207 (4)
C10	0.8699 (3)	0.5819 (2)	0.32888 (15)	0.0229 (4)
H10A	0.7941	0.5190	0.3120	0.027*
H10B	0.9937	0.5147	0.3458	0.027*
C11	0.8944 (3)	0.7035 (2)	0.23948 (15)	0.0252 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0323 (2)	0.01893 (18)	0.02016 (18)	−0.00585 (14)	0.00617 (14)	−0.00096 (13)
Zn2	0.02595 (14)	0.02400 (14)	0.02075 (13)	−0.00288 (10)	0.00454 (10)	−0.00511 (10)
O1	0.0366 (9)	0.0184 (7)	0.0240 (8)	−0.0050 (6)	0.0098 (6)	−0.0014 (6)
O2	0.0328 (9)	0.0246 (8)	0.0268 (8)	−0.0082 (7)	0.0064 (6)	0.0040 (6)
O3	0.0374 (9)	0.0147 (7)	0.0220 (7)	−0.0049 (6)	0.0101 (6)	−0.0030 (6)
O4	0.0319 (8)	0.0261 (8)	0.0195 (7)	0.0005 (6)	0.0040 (6)	−0.0029 (6)
O5	0.0313 (8)	0.0226 (8)	0.0239 (8)	0.0038 (6)	0.0003 (6)	−0.0055 (6)
O6	0.0405 (9)	0.0179 (7)	0.0188 (7)	−0.0066 (6)	0.0097 (6)	−0.0032 (6)
O7	0.0838 (14)	0.0222 (8)	0.0266 (8)	−0.0166 (9)	0.0076 (9)	−0.0024 (7)
O8	0.0445 (10)	0.0279 (8)	0.0183 (7)	−0.0088 (7)	0.0053 (7)	−0.0042 (6)
O1w	0.0403 (10)	0.0250 (9)	0.0313 (9)	−0.0059 (7)	−0.0043 (7)	−0.0042 (7)
O2w	0.0313 (10)	0.0245 (9)	0.0532 (11)	−0.0030 (7)	0.0090 (8)	0.0067 (8)
O3w	0.0348 (9)	0.0224 (8)	0.0419 (10)	−0.0070 (7)	−0.0044 (8)	−0.0042 (7)
O4w	0.0290 (9)	0.0576 (12)	0.0245 (8)	−0.0037 (9)	0.0030 (7)	0.0043 (8)
O5w	0.0289 (9)	0.0415 (10)	0.0262 (8)	−0.0127 (7)	0.0045 (7)	−0.0112 (7)
O6w	0.0391 (17)	0.0333 (16)	0.0384 (17)	0.0018 (12)	−0.0112 (13)	−0.0101 (13)
O6w'	0.065 (5)	0.049 (4)	0.074 (5)	0.001 (3)	−0.031 (4)	−0.018 (4)
C1	0.0242 (11)	0.0210 (10)	0.0212 (10)	−0.0068 (8)	−0.0014 (8)	−0.0011 (8)
C2	0.0355 (13)	0.0222 (11)	0.0262 (11)	−0.0072 (9)	0.0113 (9)	−0.0011 (9)
C3	0.0224 (10)	0.0157 (9)	0.0213 (10)	−0.0019 (8)	0.0000 (8)	−0.0042 (8)
C4	0.0246 (10)	0.0206 (10)	0.0181 (10)	−0.0049 (8)	0.0030 (8)	−0.0010 (8)
C5	0.0207 (10)	0.0199 (10)	0.0199 (10)	−0.0024 (8)	−0.0008 (8)	−0.0059 (8)
C6	0.0246 (10)	0.0168 (10)	0.0217 (10)	−0.0027 (8)	−0.0005 (8)	−0.0042 (8)
C7	0.0237 (10)	0.0205 (10)	0.0178 (10)	−0.0061 (8)	0.0013 (8)	−0.0019 (8)
C8	0.0248 (10)	0.0209 (10)	0.0180 (10)	−0.0038 (8)	0.0039 (8)	−0.0048 (8)
C9	0.0219 (10)	0.0208 (10)	0.0205 (10)	−0.0062 (8)	0.0016 (8)	−0.0068 (8)
C10	0.0278 (11)	0.0208 (10)	0.0196 (10)	−0.0061 (8)	0.0034 (8)	−0.0059 (8)
C11	0.0296 (11)	0.0220 (11)	0.0223 (11)	−0.0062 (9)	0.0012 (9)	−0.0019 (8)

Geometric parameters (Å, º)

Zn1—O1	1.9744 (14)	O2w—H2w2	0.84 (1)
Zn1—O1^i	1.9744 (14)	O3w—H3w1	0.84 (1)
Zn1—O1w	2.1078 (16)	O3w—H3w2	0.85 (3)
Zn1—O1w^i	2.1078 (16)	O4w—H4w1	0.86 (3)
Zn1—O3^i	2.2742 (14)	O4w—H4w2	0.85 (1)
Zn1—O3	2.2742 (14)	O5w—H5w1	0.85 (1)
Zn2—O4w	2.0194 (16)	O5w—H5w2	0.85 (1)
Zn2—O2w	2.0566 (16)	O6w—H6w1	0.85 (1)
Zn2—O3w	2.0771 (16)	O6w—H6w2	0.86 (1)
Zn2—O5w	2.1091 (16)	C1—C2	1.518 (3)
Zn2—O4	2.1242 (15)	C2—H2A	0.9700
Zn2—O5	2.2347 (14)	C2—H2B	0.9700
O1—C1	1.251 (2)	C3—C4	1.380 (3)
O2—C1	1.244 (2)	C3—C8	1.384 (3)
O3—C3	1.392 (2)	C4—C5	1.393 (3)
O3—C2	1.429 (2)	C4—H4	0.9300
O4—C9	1.272 (2)	C5—C6	1.381 (3)
O5—C9	1.255 (2)	C5—C9	1.488 (3)
O6—C7	1.371 (2)	C6—C7	1.389 (3)
O6—C10	1.425 (2)	C6—H6	0.9300
O7—C11	1.233 (3)	C7—C8	1.378 (3)
O8—C11	1.271 (2)	C8—H8	0.9300
O1w—H1w1	0.85 (1)	C10—C11	1.503 (3)
O1w—H1w2	0.85 (1)	C10—H10A	0.9700
O2w—H2w1	0.84 (1)	C10—H10B	0.9700
O1—Zn1—O1^i	180.0	Zn2—O4w—H4w2	115.9 (18)
O1—Zn1—O1w	90.41 (6)	H4w1—O4w—H4w2	108.3 (15)
O1^i—Zn1—O1w	89.59 (6)	Zn2—O5w—H5w1	114.5 (17)
O1—Zn1—O1w^i	89.59 (6)	Zn2—O5w—H5w2	116 (2)
O1^i—Zn1—O1w^i	90.41 (6)	H5w1—O5w—H5w2	108.2 (15)
O1w—Zn1—O1w^i	180.00 (7)	H6w1—O6w—H6w2	107.9 (17)
O1—Zn1—O3^i	102.88 (5)	H6w1—O6w'—H6w2	67.6 (17)
O1^i—Zn1—O3^i	77.12 (5)	O2—C1—O1	124.92 (19)
O1w—Zn1—O3^i	91.35 (6)	O2—C1—C2	115.08 (18)
O1w^i—Zn1—O3^i	88.65 (6)	O1—C1—C2	119.98 (17)
O1—Zn1—O3	77.12 (5)	O3—C2—C1	110.61 (17)
O1^i—Zn1—O3	102.88 (5)	O3—C2—H2A	109.5
O1w—Zn1—O3	88.65 (6)	C1—C2—H2A	109.5
O1w^i—Zn1—O3	91.35 (6)	O3—C2—H2B	109.5
O3^i—Zn1—O3	180.00 (5)	C1—C2—H2B	109.5
O4w—Zn2—O2w	99.31 (8)	H2A—C2—H2B	108.1
O4w—Zn2—O3w	94.63 (7)	C4—C3—C8	121.46 (18)
O2w—Zn2—O3w	85.62 (7)	C4—C3—O3	123.55 (18)
O4w—Zn2—O5w	88.50 (7)	C8—C3—O3	114.99 (17)
O2w—Zn2—O5w	89.36 (7)	C3—C4—C5	118.54 (18)
O3w—Zn2—O5w	174.46 (6)	C3—C4—H4	120.7
O4w—Zn2—O4	103.16 (7)	C5—C4—H4	120.7
O2w—Zn2—O4	157.52 (7)	C6—C5—C4	120.94 (18)
O3w—Zn2—O4	91.76 (6)	C6—C5—C9	120.35 (18)
O5w—Zn2—O4	91.97 (6)	C4—C5—C9	118.68 (18)
O4w—Zn2—O5	161.01 (6)	C5—C6—C7	119.11 (18)
O2w—Zn2—O5	97.82 (6)	C5—C6—H6	120.4
O3w—Zn2—O5	94.79 (6)	C7—C6—H6	120.4
O5w—Zn2—O5	83.55 (6)	O6—C7—C8	123.42 (17)
O4—Zn2—O5	60.09 (5)	O6—C7—C6	115.68 (17)
C1—O1—Zn1	121.99 (13)	C8—C7—C6	120.90 (18)
C3—O3—C2	116.78 (15)	C7—C8—C3	119.02 (18)
C3—O3—Zn1	132.71 (12)	C7—C8—H8	120.5
C2—O3—Zn1	110.27 (11)	C3—C8—H8	120.5
C9—O4—Zn2	92.45 (11)	O5—C9—O4	119.59 (18)
C9—O5—Zn2	87.87 (12)	O5—C9—C5	120.62 (17)
C7—O6—C10	116.56 (15)	O4—C9—C5	119.76 (17)
Zn1—O1w—H1w1	110 (2)	O6—C10—C11	109.57 (17)
Zn1—O1w—H1w2	113 (2)	O6—C10—H10A	109.8
H1w1—O1w—H1w2	109.8 (16)	C11—C10—H10A	109.8
Zn2—O2w—H2w1	118.4 (18)	O6—C10—H10B	109.8
Zn2—O2w—H2w2	128.7 (19)	C11—C10—H10B	109.8
H2w1—O2w—H2w2	111.9 (16)	H10A—C10—H10B	108.2
Zn2—O3w—H3w1	120.8 (17)	O7—C11—O8	125.04 (19)
Zn2—O3w—H3w2	111.1 (19)	O7—C11—C10	120.39 (19)
H3w1—O3w—H3w2	109.7 (15)	O8—C11—C10	114.55 (18)
Zn2—O4w—H4w1	124 (2)
O1w—Zn1—O1—C1	−88.19 (16)	Zn1—O3—C3—C4	−166.41 (14)
O1w^i—Zn1—O1—C1	91.81 (16)	C2—O3—C3—C8	−172.49 (17)
O3^i—Zn1—O1—C1	−179.67 (15)	Zn1—O3—C3—C8	13.7 (3)
O3—Zn1—O1—C1	0.33 (15)	C8—C3—C4—C5	1.8 (3)
O1—Zn1—O3—C3	172.76 (18)	O3—C3—C4—C5	−177.99 (18)
O1^i—Zn1—O3—C3	−7.24 (18)	C3—C4—C5—C6	−0.9 (3)
O1w—Zn1—O3—C3	−96.51 (17)	C3—C4—C5—C9	177.00 (17)
O1w^i—Zn1—O3—C3	83.49 (17)	C4—C5—C6—C7	−0.7 (3)
O1—Zn1—O3—C2	−1.31 (13)	C9—C5—C6—C7	−178.56 (18)
O1^i—Zn1—O3—C2	178.69 (13)	C10—O6—C7—C8	6.0 (3)
O1w—Zn1—O3—C2	89.42 (14)	C10—O6—C7—C6	−173.57 (17)
O1w^i—Zn1—O3—C2	−90.58 (14)	C5—C6—C7—O6	−179.03 (17)
O4w—Zn2—O4—C9	−169.99 (12)	C5—C6—C7—C8	1.4 (3)
O2w—Zn2—O4—C9	12.0 (2)	O6—C7—C8—C3	180.00 (17)
O3w—Zn2—O4—C9	94.84 (12)	C6—C7—C8—C3	−0.5 (3)
O5w—Zn2—O4—C9	−81.07 (12)	C4—C3—C8—C7	−1.2 (3)
O5—Zn2—O4—C9	0.33 (11)	O3—C3—C8—C7	178.66 (18)
O4w—Zn2—O5—C9	29.9 (3)	Zn2—O5—C9—O4	0.56 (18)
O2w—Zn2—O5—C9	−175.84 (12)	Zn2—O5—C9—C5	178.66 (17)
O3w—Zn2—O5—C9	−89.61 (12)	Zn2—O4—C9—O5	−0.58 (19)
O5w—Zn2—O5—C9	95.70 (12)	Zn2—O4—C9—C5	−178.70 (16)
O4—Zn2—O5—C9	−0.33 (11)	C6—C5—C9—O5	24.9 (3)
Zn1—O1—C1—O2	−177.86 (15)	C4—C5—C9—O5	−152.95 (19)
Zn1—O1—C1—C2	0.7 (3)	C6—C5—C9—O4	−156.98 (18)
C3—O3—C2—C1	−173.21 (17)	C4—C5—C9—O4	25.1 (3)
Zn1—O3—C2—C1	1.9 (2)	C7—O6—C10—C11	175.12 (16)
O2—C1—C2—O3	176.85 (17)	O6—C10—C11—O7	16.0 (3)
O1—C1—C2—O3	−1.9 (3)	O6—C10—C11—O8	−165.57 (17)
C2—O3—C3—C4	7.4 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O5^ii	0.85 (1)	1.95 (1)	2.786 (2)	170 (3)
O1w—H1w2···O7^iii	0.85 (1)	2.10 (2)	2.836 (2)	145 (3)
O2w—H2w1···O7^iv	0.84 (1)	1.82 (1)	2.657 (2)	172 (3)
O2w—H2w2···O6w	0.84 (1)	2.09 (2)	2.843 (4)	150 (3)
O3w—H3w1···O8^ii	0.84 (1)	1.93 (1)	2.761 (2)	167 (2)
O3w—H3w2···O2^v	0.85 (3)	1.93 (1)	2.772 (2)	172 (3)
O4w—H4w1···O4^vi	0.86 (3)	1.91 (1)	2.758 (2)	173 (3)
O4w—H4w2···O8^vii	0.85 (1)	1.81 (1)	2.655 (2)	180 (3)
O5w—H5w1···O2^viii	0.85 (1)	1.84 (1)	2.685 (2)	170 (2)
O5w—H5w2···O6w^ix	0.85 (1)	1.97 (2)	2.708 (3)	144 (3)
O5w—H5w2···O6w′^ix	0.85 (1)	1.90 (1)	2.732 (6)	168 (3)
O6w—H6w1···O8^vii	0.85 (1)	1.94 (2)	2.747 (3)	158 (4)
O6w—H6w2···O5w^x	0.86 (1)	1.98 (2)	2.791 (3)	156 (4)

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+2, −z+1; (v) x−1, y+1, z; (vi) −x+1, −y+1, −z+2; (vii) x−1, y, z+1; (viii) x, y+1, z; (ix) x+1, y, z; (x) −x, −y+2, −z+2.