Calcium(II) meso-2,3-di­phenyl­succinate heptahydrate

The title compound, [Ca(C₁₆H₁₂O₄)(H₂O)₆]·H₂O, adopts a conformation about the central C—C bond that places the two carboxylate groups in an anti orientation. The crystal consists of layers of two-dimensional arrays of 2,3-di­phenyl­succinate dianions which are linked by bridging Ca²⁺ cations. The unit cell contains two Ca²⁺ cations in an unusual four-membered Ca—O—Ca—O ring in which the bridging O atoms belong to water mol­ecules rather than carboxyl­ates, i.e. poly­[[[di-μ-aqua-bis­[penta­aqua­calcium(II)]]-μ-(meso-2,3-di­phenyl­succinato-O:O′)] succinate dihydrate].

S1. Comment

As part of our ongoing study of shape-switchable molecules (Monahan et al., 1998), we have examined some of the structural and environmental factors that control the conformation of meso-2,3-succinate derivatives (^-O₂CCHXCHXCO₂^-). In the case of X = OH (meso-tartrate), previous NMR evidence indicates that in aqueous solution the dianion adopts a conformation with the carboxylate groups in a gauche arrangement when the molecule is viewed along the central C2—C3 bond (Ascenso & Gil, 1980). It was of interest to know if other derivatives adopted, or could be forced to adopt, the same unusual conformation. The conformations in alkaline solution were assigned from vicinal H—H coupling constants (³J_HH). In the case of X = OCH₃, ³J_HH = 5.5 Hz, which indicates that a gauche conformation is predominant (Ascenso & Gil, 1980). In the case of X = Br and X = Ph, the ³J_HH values of 11.4 and 12.5 Hz, respectively, suggest conformations with the carboxylate groups in an anti orientation. In the case of X = Ph, attempts were made to induce a conformational change to gauche by adding CaCl₂ or MgCl₂ to the basic aqueous solutions. In both cases, there were only minor changes in ³J_HH values (<0.5 Hz) indicating that even in the presence of chelating dications, meso-2,3-diphenylsuccinate remains in an anti conformation. Since this result is counter to that obtained with a related sysytem (Monahan et al., 1998), we decided to confirm our structural assignments with an X-ray analysis of the title crystalline calcium meso-2,3-diphenylsuccinate, (I). \scheme

The crystal structures of a number of succinate salts are known, including the mono- and trihydrates of calcium succinate (Karipides & Reed, 1980; Mathew et al., 1994). However, this is the first reported structure of a 2,3-diphenylsuccinate salt. X-ray analysis of (I) shows that the molecule adopts an anti conformation about the C2—C3 bond (Fig. 1). The crystal consists of layers of a two-dimensional array of succinate dianions that are linked by bridging Ca²⁺ ions. Along one axis, the carboxylates are directly bonded to the Ca²⁺ ions, whereas along the other axis they are hydrogen bonded to bridging water molecules. The phenyl rings pack in face-to-face and edge-to-face orientations to form square-shaped nanotubes with aromatic walls, and the interiors of the tubes contain the hydrated calcium carboxylate ion pairs.

The literature structures of calcium succinate show the Ca and the carboxylate O atoms in two types of four-membered rings (Karipides & Reed, 1980; Mathew et al., 1994). Either a carboxylate group forms a bidentate Ca—O—C—O ring, or it provides a bridging unidentate O atom which is part of a four-membered Ca—O—Ca—O ring. As shown in Fig. 1, compound (I) forms a different type of Ca—O—Ca—O ring in which the bridging O atoms belong to water molecules rather than to carboxylates. The internuclear Ca—Ca distance is 4.3110 (7) Å; which is longer than the 3.98–4.01 Å found in the literature succinate Ca—O—Ca—O rings (Karipides & Reed, 1980; Mathew et al., 1994).

S2. Experimental

meso-2,3-Diphenylsuccinic acid (182 mg, 0.673 mmol), synthesized according to the method of Wawzonek (1940), was added to solution of Ca(OH)₂ (50 mg, 0.673 mmol) in water (100 ml). Slow evaporation of the water produced satisfactory crystals of (I).

S3. Refinement

Phenyl H atoms were refined with a riding model. All other H atoms were refined with a free variable to restrain H—O and H—H distances.

Computing details

Data collection: CAD-4 ARGUS (Enraf-Nonius, 1994); cell refinement: CAD-4 ARGUS; data reduction: CHI90S (Boyle, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Siemens, 1994).

Figures

Fig. 1. The representation of the unit cell of (I), drawn with 40% probability displacement ellipsoids. The uncoordinated water molecules and non-aqueous H atoms are not shown [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, -z].

Calcium(II) meso-2,3-diphenylsuccinate heptahydrate

Crystal data

[Ca(C16H12O4)(H2O)6]·H2O	Z = 2
Mr = 434.45	F(000) = 460
Triclinic, P1	Dx = 1.420 Mg m^−3
a = 6.2394 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6342 (8) Å	Cell parameters from 25 reflections
c = 14.1648 (12) Å	θ = 15–16°
α = 89.697 (7)°	µ = 0.36 mm^−1
β = 88.440 (9)°	T = 293 K
γ = 81.320 (8)°	Plate-like, colorless
V = 1016.1 (2) Å^3	0.42 × 0.40 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3307 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.010
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
θ/2θ scans	h = −7→0
Absorption correction: ψ-scan (North et al., 1968)	k = −13→13
Tmin = 0.922, Tmax = 0.947	l = −16→16
3939 measured reflections	3 standard reflections every 200 reflections
3580 independent reflections	intensity decay: none

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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Calculated w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 0.5761P] where P = (Fo^2 + 2Fc^2)/3
3580 reflections	(Δ/σ)max = −0.001
305 parameters	Δρmax = 0.32 e Å^−3
27 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. North A·C·T., Phillips D·C. & Mathews F·S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7. Theta correction was applied. Weighted transmission curves were used. No Fourier smoothing was applied.

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_obs 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ca	0.37991 (5)	0.47407 (3)	0.36167 (2)	0.02282 (11)
O1	0.2858 (2)	0.53681 (11)	0.53998 (9)	0.0273 (3)
H11	0.201 (3)	0.4974 (16)	0.5640 (14)	0.033*
H12	0.221 (3)	0.6022 (16)	0.5413 (14)	0.033*
O2	0.3643 (2)	0.29612 (11)	0.45747 (9)	0.0301 (3)
H21	0.454 (3)	0.2439 (17)	0.4399 (15)	0.036*
H22	0.250 (3)	0.2711 (18)	0.4574 (15)	0.036*
O3	0.4686 (2)	0.66553 (11)	0.37107 (10)	0.0363 (3)
H31	0.517 (4)	0.6937 (19)	0.4153 (14)	0.044*
H32	0.445 (4)	0.7134 (19)	0.3335 (14)	0.044*
O4	0.0164 (2)	0.59266 (12)	0.37396 (9)	0.0323 (3)
H41	−0.046 (3)	0.6081 (18)	0.3242 (14)	0.039*
H42	0.021 (4)	0.6506 (17)	0.3990 (14)	0.039*
O5	0.6662 (2)	0.32689 (13)	0.28615 (10)	0.0416 (3)
H51	0.686 (4)	0.2639 (19)	0.3128 (15)	0.050*
H52	0.639 (4)	0.315 (2)	0.2352 (14)	0.050*
O6	0.1447 (2)	0.36844 (14)	0.27377 (10)	0.0434 (4)
H61	0.138 (4)	0.399 (2)	0.2215 (15)	0.052*
H62	0.035 (4)	0.351 (2)	0.2846 (17)	0.052*
O7	0.4400 (2)	0.53731 (11)	0.20218 (8)	0.0330 (3)
C1	0.3591 (3)	0.52495 (15)	0.12349 (12)	0.0279 (4)
O8	0.1779 (2)	0.49517 (13)	0.11197 (9)	0.0401 (3)
C2	0.4933 (3)	0.5502 (2)	0.03496 (12)	0.0315 (4)
H2A	0.6407	0.5561	0.05444	0.038*
C3	0.3991 (3)	0.6655 (2)	−0.01053 (13)	0.0348 (4)
C4	0.1878 (3)	0.6888 (2)	−0.04200 (15)	0.0440 (5)
H4A	0.0974	0.6323	−0.03646	0.053*
C5	0.1115 (4)	0.7957 (2)	−0.0815 (2)	0.0584 (6)
H5A	−0.0304	0.8110	−0.1019	0.070*
C6	0.2447 (5)	0.8795 (2)	−0.0908 (2)	0.0681 (8)
H6A	0.1928	0.9517	−0.1167	0.082*
C7	0.4537 (5)	0.8557 (2)	−0.0617 (2)	0.0630 (7)
H7A	0.5447	0.9118	−0.0686	0.076*
C8	0.5308 (4)	0.7499 (2)	−0.0222 (2)	0.0473 (5)
H8A	0.6738	0.7349	−0.0032	0.057*
O11	0.7241 (2)	0.14112 (11)	0.41269 (11)	0.0408 (3)
C11	0.8902 (3)	0.1541 (2)	0.45469 (14)	0.0344 (4)
C12A	0.9960 (6)	0.0581 (3)	0.5249 (3)	0.0271 (7)	0.50
H12A	1.1446	0.0710	0.5366	0.032*	0.50
C12B	1.0542 (6)	0.0382 (3)	0.4654 (3)	0.0306 (8)	0.50
H12B	1.1855	0.0571	0.4942	0.037*	0.50
O12	0.9558 (2)	0.24924 (10)	0.46731 (10)	0.0362 (3)
C13	0.8740 (4)	0.0448 (3)	0.6234 (2)	0.0581 (7)
C14	0.6745 (4)	0.0199 (2)	0.6484 (2)	0.0614 (7)
H14A	0.5990	−0.0199	0.6070	0.074*
C15	0.5850 (5)	0.0540 (4)	0.7355 (3)	0.1023 (15)
H15A	0.4484	0.0373	0.7533	0.123*
C16	0.6961 (10)	0.1120 (4)	0.7953 (2)	0.120 (2)
H16A	0.6357	0.1341	0.8544	0.144*
C17	0.8890 (9)	0.1374 (2)	0.7708 (2)	0.0993 (15)
H17A	0.9627	0.1783	0.8122	0.119*
C18	0.9791 (5)	0.1043 (3)	0.6861 (2)	0.0765 (9)
H18A	1.1156	0.1223	0.6697	0.092*
O21	−0.1697 (3)	0.6331 (2)	0.20785 (11)	0.0480 (4)
H211	−0.277 (4)	0.605 (2)	0.2053 (18)	0.058*
H212	−0.082 (4)	0.594 (2)	0.1728 (17)	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca	0.0227 (2)	0.0244 (2)	0.0212 (2)	−0.00323 (13)	−0.00017 (12)	0.00170 (12)
O1	0.0245 (6)	0.0241 (6)	0.0320 (6)	−0.0004 (5)	0.0016 (5)	0.0026 (5)
O2	0.0294 (7)	0.0267 (6)	0.0340 (7)	−0.0043 (5)	0.0007 (5)	−0.0011 (5)
O3	0.0502 (8)	0.0299 (7)	0.0303 (7)	−0.0098 (6)	−0.0082 (6)	0.0042 (5)
O4	0.0293 (7)	0.0373 (7)	0.0301 (7)	−0.0034 (6)	−0.0042 (5)	−0.0029 (6)
O5	0.0491 (8)	0.0423 (8)	0.0301 (7)	0.0026 (7)	0.0034 (6)	0.0021 (6)
O6	0.0486 (9)	0.0536 (9)	0.0337 (7)	−0.0257 (7)	−0.0045 (7)	0.0055 (6)
O7	0.0368 (7)	0.0444 (7)	0.0198 (6)	−0.0126 (6)	−0.0005 (5)	0.0026 (5)
C1	0.0316 (9)	0.0289 (9)	0.0230 (8)	−0.0048 (7)	0.0041 (7)	0.0002 (7)
O8	0.0354 (7)	0.0630 (9)	0.0250 (6)	−0.0179 (6)	0.0008 (5)	0.0016 (6)
C2	0.0301 (9)	0.0423 (10)	0.0231 (8)	−0.0093 (8)	0.0017 (7)	−0.0007 (7)
C3	0.0406 (10)	0.0350 (10)	0.0276 (9)	−0.0038 (8)	0.0088 (8)	0.0003 (7)
C4	0.0418 (11)	0.0463 (12)	0.0436 (11)	−0.0062 (9)	0.0013 (9)	0.0059 (9)
C5	0.0503 (13)	0.064 (2)	0.0550 (14)	0.0098 (11)	0.0008 (11)	0.0172 (12)
C6	0.079 (2)	0.0422 (13)	0.075 (2)	0.0115 (12)	0.0175 (14)	0.0238 (12)
C7	0.075 (2)	0.0389 (12)	0.076 (2)	−0.0171 (12)	0.0137 (14)	0.0101 (11)
C8	0.0455 (12)	0.0465 (12)	0.0513 (13)	−0.0123 (10)	0.0038 (10)	0.0068 (10)
O11	0.0352 (7)	0.0252 (6)	0.0610 (9)	−0.0007 (5)	−0.0093 (6)	−0.0001 (6)
C11	0.0258 (9)	0.0261 (9)	0.0496 (11)	0.0010 (7)	0.0000 (8)	0.0102 (8)
C12A	0.025 (2)	0.024 (2)	0.032 (2)	−0.0028 (14)	0.000 (2)	−0.002 (2)
C12B	0.028 (2)	0.023 (2)	0.039 (2)	0.0003 (15)	−0.003 (2)	0.001 (2)
O12	0.0315 (7)	0.0254 (6)	0.0514 (8)	−0.0028 (5)	−0.0025 (6)	0.0039 (6)
C13	0.0366 (11)	0.099 (2)	0.0322 (11)	0.0106 (12)	0.0001 (9)	−0.0128 (11)
C14	0.0472 (13)	0.0386 (12)	0.098 (2)	−0.0044 (10)	−0.0095 (13)	−0.0065 (12)
C15	0.065 (2)	0.112 (3)	0.117 (3)	0.017 (2)	0.049 (2)	0.067 (3)
C16	0.191 (5)	0.100 (3)	0.041 (2)	0.067 (3)	0.030 (3)	0.009 (2)
C17	0.208 (5)	0.0410 (14)	0.051 (2)	−0.016 (2)	−0.051 (2)	−0.0006 (13)
C18	0.075 (2)	0.106 (2)	0.060 (2)	−0.048 (2)	−0.0282 (14)	0.039 (2)
O21	0.0359 (8)	0.0702 (11)	0.0399 (8)	−0.0140 (7)	−0.0020 (6)	−0.0037 (7)

Geometric parameters (Å, º)

Ca—O3	2.3799 (13)	C5—C6	1.377 (4)
Ca—O7	2.4093 (12)	C6—C7	1.367 (4)
Ca—O6	2.4237 (14)	C7—C8	1.374 (3)
Ca—O4	2.4728 (13)	O11—C11	1.238 (2)
Ca—O2	2.4822 (13)	C11—O12	1.252 (2)
Ca—O5	2.5017 (15)	C11—C12A	1.572 (4)
Ca—O1^i	2.5264 (13)	C11—C12B	1.574 (4)
Ca—O1	2.6582 (13)	C12A—C12A^iii	1.522 (7)
Ca—Ca^i	4.3110 (7)	C12A—C13	1.590 (5)
O1—Ca^i	2.5264 (13)	C12B—C12B^iii	1.531 (8)
O7—C1	1.254 (2)	C12B—C13^iii	1.603 (5)
C1—O8	1.247 (2)	C13—C14	1.358 (4)
C1—C2	1.540 (2)	C13—C18	1.368 (4)
C2—C2^ii	1.526 (4)	C13—C12B^iii	1.603 (5)
C2—C3	1.528 (3)	C14—C15	1.375 (5)
C3—C8	1.379 (3)	C15—C16	1.353 (7)
C3—C4	1.390 (3)	C16—C17	1.319 (6)
C4—C5	1.384 (3)	C17—C18	1.345 (5)
O3—Ca—O7	73.03 (5)	C1—O7—Ca	136.09 (11)
O3—Ca—O6	138.96 (5)	O8—C1—O7	124.8 (2)
O7—Ca—O6	78.01 (5)	O8—C1—C2	117.97 (15)
O3—Ca—O4	78.32 (5)	O7—C1—C2	117.2 (2)
O7—Ca—O4	92.66 (5)	C2^ii—C2—C3	111.3 (2)
O6—Ca—O4	74.60 (5)	C2^ii—C2—C1	110.1 (2)
O3—Ca—O2	142.01 (5)	C3—C2—C1	111.14 (14)
O7—Ca—O2	141.86 (4)	C8—C3—C4	118.4 (2)
O6—Ca—O2	76.27 (5)	C8—C3—C2	118.4 (2)
O4—Ca—O2	106.93 (5)	C4—C3—C2	123.1 (2)
O3—Ca—O5	115.20 (5)	C5—C4—C3	120.3 (2)
O7—Ca—O5	72.39 (5)	C6—C5—C4	120.3 (2)
O6—Ca—O5	81.81 (5)	C7—C6—C5	119.4 (2)
O4—Ca—O5	154.35 (5)	C6—C7—C8	120.7 (2)
O2—Ca—O5	76.44 (5)	C7—C8—C3	120.9 (2)
O3—Ca—O1^i	72.66 (5)	O11—C11—O12	125.3 (2)
O7—Ca—O1^i	112.62 (4)	O11—C11—C12A	120.4 (2)
O6—Ca—O1^i	146.96 (5)	O12—C11—C12A	111.7 (2)
O4—Ca—O1^i	132.88 (4)	O11—C11—C12B	113.5 (2)
O2—Ca—O1^i	77.50 (4)	O12—C11—C12B	118.9 (2)
O5—Ca—O1^i	72.76 (5)	C12A^iii—C12A—C11	106.6 (4)
O3—Ca—O1	75.66 (4)	C12A^iii—C12A—C13	105.6 (4)
O7—Ca—O1	146.65 (4)	C11—C12A—C13	117.8 (3)
O6—Ca—O1	121.18 (5)	C12B^iii—C12B—C11	106.2 (4)
O4—Ca—O1	69.83 (4)	C12B^iii—C12B—C13^iii	104.3 (4)
O2—Ca—O1	71.48 (4)	C11—C12B—C13^iii	121.1 (3)
O5—Ca—O1	133.04 (4)	C14—C13—C18	118.5 (2)
O1^i—Ca—O1	67.52 (4)	C14—C13—C12A	133.7 (2)
O3—Ca—Ca^i	70.89 (4)	C18—C13—C12A	104.6 (2)
O7—Ca—Ca^i	137.77 (3)	C14—C13—C12B^iii	103.7 (2)
O6—Ca—Ca^i	144.14 (4)	C18—C13—C12B^iii	135.4 (3)
O4—Ca—Ca^i	100.73 (3)	C13—C14—C15	119.5 (3)
O2—Ca—Ca^i	71.18 (3)	C16—C15—C14	119.9 (3)
O5—Ca—Ca^i	104.31 (4)	C17—C16—C15	120.8 (3)
O1^i—Ca—Ca^i	34.73 (3)	C16—C17—C18	120.1 (3)
O1—Ca—Ca^i	32.79 (3)	C17—C18—C13	121.3 (3)
Ca^i—O1—Ca	112.48 (4)
O3—Ca—O1—Ca	−76.87 (6)	C6—C7—C8—C3	−0.5 (4)
O7—Ca—O1—Ca	−97.38 (8)	C4—C3—C8—C7	1.8 (3)
O6—Ca—O1—Ca	144.09 (6)	C2—C3—C8—C7	−179.2 (2)
O4—Ca—O1—Ca	−159.47 (6)	O11—C11—C12A—C12A	46.2 (4)
O2—Ca—O1—Ca	83.77 (5)	O12—C11—C12A—C12A	−151.4 (3)
O5—Ca—O1—Ca	34.38 (8)	C12B—C11—C12A—C12A	−41.5 (3)
O1—Ca—O1—Ca	0.0	O11—C11—C12A—C13	−72.2 (3)
Ca—Ca—O1—Ca	0.0	O12—C11—C12A—C13	90.3 (3)
O3—Ca—O7—C1	−143.4 (2)	C12B—C11—C12A—C13	−159.9 (5)
O6—Ca—O7—C1	7.2 (2)	O11—C11—C12B—C12B	−68.9 (4)
O4—Ca—O7—C1	−66.5 (2)	O12—C11—C12B—C12B	127.6 (3)
O2—Ca—O7—C1	55.6 (2)	C12A—C11—C12B—C12B	41.1 (3)
O5—Ca—O7—C1	92.3 (2)	O11—C11—C12B—C13	49.5 (3)
O1—Ca—O7—C1	154.3 (2)	O12—C11—C12B—C13	−114.1 (3)
O1—Ca—O7—C1	−122.6 (2)	C12A—C11—C12B—C13	159.4 (5)
Ca—Ca—O7—C1	−175.64 (14)	C12A—C12A—C13—C14	−59.0 (5)
Ca—O7—C1—O8	18.9 (3)	C11—C12A—C13—C14	59.9 (4)
Ca—O7—C1—C2	−161.96 (12)	C12A—C12A—C13—C18	142.3 (3)
O8—C1—C2—C2	−50.4 (3)	C11—C12A—C13—C18	−98.8 (3)
O7—C1—C2—C2	130.4 (2)	C12A—C12A—C13—C12B	0.9 (3)
O8—C1—C2—C3	73.3 (2)	C11—C12A—C13—C12B	119.8 (4)
O7—C1—C2—C3	−105.9 (2)	C18—C13—C14—C15	−0.5 (4)
C2—C2—C3—C8	−114.3 (2)	C12A—C13—C14—C15	−156.8 (3)
C1—C2—C3—C8	122.7 (2)	C12B—C13—C14—C15	164.4 (3)
C2—C2—C3—C4	64.7 (3)	C13—C14—C15—C16	0.0 (5)
C1—C2—C3—C4	−58.3 (2)	C14—C15—C16—C17	0.7 (6)
C8—C3—C4—C5	−1.8 (3)	C15—C16—C17—C18	−0.9 (6)
C2—C3—C4—C5	179.2 (2)	C16—C17—C18—C13	0.4 (5)
C3—C4—C5—C6	0.6 (4)	C14—C13—C18—C17	0.3 (4)
C4—C5—C6—C7	0.8 (4)	C12A—C13—C18—C17	162.8 (3)
C5—C6—C7—C8	−0.8 (4)	C12B—C13—C18—C17	−158.6 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O4^iv	0.82 (2)	2.02 (2)	2.833 (2)	177 (2)
O1—H12···O12^i	0.81 (2)	1.91 (2)	2.712 (2)	173 (2)
O2—H21···O11	0.80 (2)	1.94 (2)	2.722 (2)	165 (2)
O2—H22···O12^v	0.81 (2)	1.89 (2)	2.686 (2)	166 (2)
O3—H31···O2^i	0.80 (2)	1.98 (2)	2.744 (2)	158 (2)
O4—H41···O21	0.82 (2)	1.84 (2)	2.660 (2)	175 (2)
O4—H42···O12^i	0.77 (2)	2.25 (2)	2.938 (2)	150 (2)
O5—H51···O11	0.82 (2)	2.00 (2)	2.788 (2)	162 (2)
O6—H61···O8	0.82 (2)	1.94 (2)	2.739 (2)	165 (2)
O6—H62···O5^v	0.75 (3)	2.36 (3)	3.096 (2)	166 (2)
O21—H211···O7^v	0.79 (2)	2.04 (2)	2.830 (2)	178 (2)
O21—H212···O8	0.82 (2)	2.02 (2)	2.817 (2)	167 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1; (v) x−1, y, z.