Aqua­(bromo­maleato-κO)­bis­(phenanthroline-κ²N,N′)­manganese(II) monohydrate

In the title complex, [Mn(C₄HBrO₄)(C₁₂H₈N₂)₂(H₂O)]·H₂O, the Mn^II atom has a distorted octahedral coordination geometry formed by two bidentate phenanthroline (phen) mol­ecules, one bromo­maleate dianion and one water mol­ecule. The large Mn—O—C bond angle of 143.31 (17)° implies poor overlap between the atomic orbitals of manganese and those of the carboxyl O atom, but despite this the Mn—O bond distance of 2.0574 (16) Å is short, suggesting a substantial electrostatic interaction in this bond. The overlapped arrangement and short face-to-face distances of 3.368 (5) and 3.501 (11) Å between neighboring parallel phen planes show π–π stacking in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.032
• wR factor = 0.081
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom C34A    has ADP max/min Ratio .............       3.20 prolat
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C34B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C32    -   C33    ...       1.31 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Aqua(bromomaleatoκ-O)bis(phenanthroline-κ²N,N')manganese(II) monohydrate

Crystal data

[Mn(C4HBrO4)(C12H8N2)2(H2O)]·H2O	F(000) = 1300
Mr = 644.34	Dx = 1.643 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8266 reflections
a = 12.2038 (4) Å	θ = 2.5–24.5°
b = 12.6561 (4) Å	µ = 2.09 mm^−1
c = 16.9518 (6) Å	T = 295 K
β = 95.714 (1)°	Prism, yellow
V = 2605.24 (15) Å^3	0.45 × 0.41 × 0.32 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 10.00 pixels mm^-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.412, Tmax = 0.516	l = −20→20
8880 measured reflections

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: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.0618P] where P = (Fo^2 + 2Fc^2)/3
4585 reflections	(Δ/σ)max = 0.001
408 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.35 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mn	0.70280 (3)	0.21241 (3)	0.54378 (2)	0.03821 (12)
BrA	0.3628 (2)	0.0624 (2)	0.80524 (15)	0.0782 (5)	0.61
O3A	0.3759 (5)	0.0776 (4)	0.6096 (3)	0.0645 (13)	0.61
O4A	0.5243 (3)	−0.0169 (3)	0.6463 (3)	0.0497 (11)	0.61
C34A	0.4515 (10)	0.0542 (10)	0.6554 (5)	0.043 (3)	0.61
BrB	0.3914 (3)	0.0340 (4)	0.8139 (3)	0.0831 (10)	0.39
O3B	0.3616 (6)	0.1462 (6)	0.6216 (5)	0.0710 (19)	0.39
O4B	0.4698 (7)	0.0096 (7)	0.6230 (5)	0.059 (2)	0.39
C34B	0.436 (2)	0.0898 (16)	0.6569 (16)	0.075 (8)	0.39
N1	0.56014 (16)	0.28036 (16)	0.46587 (11)	0.0396 (5)
N2	0.74366 (17)	0.39059 (17)	0.51870 (12)	0.0460 (5)
N3	0.80292 (16)	0.16769 (18)	0.44181 (12)	0.0463 (5)
N4	0.87980 (16)	0.19370 (17)	0.59588 (11)	0.0453 (5)
O1	0.62020 (14)	0.20385 (13)	0.64363 (10)	0.0473 (4)
O2	0.69387 (16)	0.28659 (16)	0.75173 (12)	0.0664 (6)
O5	0.64308 (14)	0.04935 (13)	0.52608 (10)	0.0480 (4)
O6A	0.7542 (4)	0.4912 (4)	0.7727 (3)	0.1006 (17)	0.61
O6B	0.8065 (8)	0.4681 (8)	0.7256 (5)	0.116 (3)	0.39
C1	0.4681 (2)	0.2281 (2)	0.44336 (15)	0.0475 (6)
H1	0.4617	0.1588	0.4605	0.057*
C2	0.3808 (2)	0.2721 (2)	0.39545 (16)	0.0530 (7)
H2	0.3181	0.2322	0.3806	0.064*
C3	0.3876 (2)	0.3723 (2)	0.37088 (15)	0.0537 (7)
H3	0.3296	0.4022	0.3386	0.064*
C4	0.4822 (2)	0.4319 (2)	0.39388 (14)	0.0454 (6)
C5	0.4943 (3)	0.5393 (2)	0.37205 (16)	0.0587 (8)
H5	0.4373	0.5729	0.3413	0.070*
C6	0.5865 (3)	0.5929 (2)	0.39506 (17)	0.0625 (9)
H6	0.5929	0.6628	0.3792	0.075*
C7	0.6757 (2)	0.5449 (2)	0.44367 (15)	0.0518 (7)
C8	0.7720 (3)	0.5980 (2)	0.47096 (19)	0.0665 (9)
H8	0.7825	0.6674	0.4554	0.080*
C9	0.8508 (3)	0.5491 (3)	0.5202 (2)	0.0703 (9)
H9	0.9155	0.5843	0.5379	0.084*
C10	0.8331 (2)	0.4447 (2)	0.54389 (17)	0.0610 (8)
H10	0.8864	0.4123	0.5788	0.073*
C11	0.6655 (2)	0.43988 (19)	0.46851 (14)	0.0412 (6)
C12	0.5678 (2)	0.38226 (19)	0.44199 (13)	0.0371 (6)
C13	0.7641 (2)	0.1515 (3)	0.36682 (16)	0.0624 (8)
H13	0.6893	0.1615	0.3524	0.075*
C14	0.8309 (3)	0.1202 (3)	0.30848 (18)	0.0764 (10)
H14	0.8009	0.1105	0.2564	0.092*
C15	0.9397 (3)	0.1042 (3)	0.32867 (19)	0.0718 (9)
H15	0.9848	0.0831	0.2904	0.086*
C16	0.9845 (2)	0.1194 (2)	0.40740 (17)	0.0532 (7)
C17	1.0983 (2)	0.1035 (2)	0.4333 (2)	0.0628 (8)
H17	1.1462	0.0818	0.3971	0.075*
C18	1.1365 (2)	0.1195 (2)	0.5088 (2)	0.0598 (8)
H18	1.2110	0.1094	0.5243	0.072*
C19	1.0655 (2)	0.1519 (2)	0.56656 (16)	0.0478 (7)
C20	1.1022 (2)	0.1688 (3)	0.64651 (18)	0.0642 (8)
H20	1.1765	0.1616	0.6640	0.077*
C21	1.0288 (2)	0.1957 (3)	0.69850 (18)	0.0708 (9)
H21	1.0524	0.2063	0.7518	0.085*
C22	0.9177 (2)	0.2074 (3)	0.67089 (16)	0.0610 (8)
H22	0.8682	0.2256	0.7070	0.073*
C23	0.95303 (19)	0.1671 (2)	0.54366 (14)	0.0397 (6)
C24	0.9117 (2)	0.15186 (19)	0.46239 (14)	0.0418 (6)
C31	0.6279 (2)	0.22502 (19)	0.71675 (15)	0.0408 (6)
C32	0.5469 (2)	0.1739 (2)	0.76509 (14)	0.0492 (7)
H32	0.5512	0.1907	0.8187	0.059*
C33	0.4704 (2)	0.1073 (2)	0.73789 (15)	0.0458 (6)
H51	0.5984	0.0270	0.5565	0.080*
H52	0.6261	0.0115	0.4822	0.080*
H61	0.7426	0.4297	0.7429	0.080*
H62	0.8295	0.4908	0.7782	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn	0.0331 (2)	0.0445 (2)	0.0362 (2)	0.00001 (17)	−0.00073 (15)	0.00318 (18)
BrA	0.0833 (12)	0.1049 (13)	0.0514 (9)	−0.0312 (8)	0.0308 (8)	−0.0082 (8)
O3A	0.050 (3)	0.089 (4)	0.052 (2)	0.004 (3)	−0.009 (2)	−0.014 (3)
O4A	0.059 (3)	0.043 (2)	0.047 (2)	0.0014 (19)	0.005 (2)	−0.0109 (17)
C34A	0.057 (5)	0.057 (8)	0.017 (4)	−0.025 (5)	0.008 (3)	−0.020 (3)
BrB	0.085 (2)	0.112 (2)	0.0542 (8)	−0.0433 (14)	0.0126 (11)	0.0140 (12)
O3B	0.041 (4)	0.093 (5)	0.075 (5)	0.000 (4)	−0.012 (3)	0.016 (5)
O4B	0.066 (6)	0.061 (5)	0.053 (5)	−0.022 (4)	0.019 (4)	−0.015 (4)
C34B	0.063 (9)	0.055 (13)	0.116 (16)	−0.037 (10)	0.055 (9)	−0.034 (9)
N1	0.0414 (12)	0.0376 (12)	0.0389 (11)	0.0024 (9)	−0.0007 (9)	0.0006 (10)
N2	0.0476 (13)	0.0489 (13)	0.0413 (12)	−0.0092 (11)	0.0038 (10)	−0.0035 (10)
N3	0.0442 (12)	0.0569 (13)	0.0378 (12)	−0.0085 (11)	0.0041 (10)	0.0010 (10)
N4	0.0369 (11)	0.0587 (15)	0.0401 (12)	0.0015 (10)	0.0020 (9)	0.0064 (10)
O1	0.0505 (10)	0.0529 (11)	0.0392 (10)	−0.0068 (9)	0.0074 (8)	−0.0018 (8)
O2	0.0621 (12)	0.0700 (14)	0.0647 (13)	−0.0229 (11)	−0.0056 (10)	−0.0125 (11)
O5	0.0521 (11)	0.0462 (10)	0.0470 (10)	−0.0072 (8)	0.0104 (8)	−0.0077 (8)
O6A	0.101 (4)	0.060 (3)	0.128 (4)	−0.022 (3)	−0.050 (3)	0.015 (3)
O6B	0.135 (8)	0.113 (7)	0.094 (6)	−0.054 (6)	−0.018 (5)	0.015 (5)
C1	0.0456 (15)	0.0432 (16)	0.0522 (16)	−0.0009 (12)	−0.0034 (12)	−0.0055 (13)
C2	0.0419 (15)	0.065 (2)	0.0499 (16)	0.0022 (14)	−0.0074 (12)	−0.0109 (15)
C3	0.0532 (17)	0.068 (2)	0.0383 (14)	0.0202 (15)	−0.0041 (13)	0.0004 (14)
C4	0.0578 (17)	0.0485 (16)	0.0309 (12)	0.0154 (13)	0.0089 (12)	0.0011 (12)
C5	0.082 (2)	0.0540 (19)	0.0419 (15)	0.0204 (17)	0.0146 (15)	0.0112 (14)
C6	0.102 (3)	0.0390 (16)	0.0518 (17)	0.0163 (17)	0.0326 (18)	0.0145 (14)
C7	0.073 (2)	0.0398 (15)	0.0465 (15)	−0.0056 (14)	0.0277 (15)	−0.0043 (13)
C8	0.089 (2)	0.0460 (17)	0.070 (2)	−0.0138 (17)	0.0358 (19)	−0.0026 (16)
C9	0.071 (2)	0.066 (2)	0.077 (2)	−0.0330 (18)	0.0252 (19)	−0.0225 (18)
C10	0.0558 (18)	0.064 (2)	0.0626 (19)	−0.0160 (15)	0.0032 (15)	−0.0100 (16)
C11	0.0545 (16)	0.0379 (14)	0.0331 (13)	0.0011 (12)	0.0141 (12)	−0.0004 (11)
C12	0.0491 (15)	0.0366 (14)	0.0265 (11)	0.0049 (11)	0.0075 (11)	−0.0008 (10)
C13	0.0579 (18)	0.084 (2)	0.0451 (17)	−0.0171 (16)	0.0037 (14)	0.0003 (16)
C14	0.078 (2)	0.108 (3)	0.0450 (17)	−0.037 (2)	0.0155 (16)	−0.0172 (18)
C15	0.077 (2)	0.084 (2)	0.0595 (19)	−0.0301 (19)	0.0306 (17)	−0.0215 (17)
C16	0.0538 (17)	0.0471 (16)	0.0620 (18)	−0.0143 (13)	0.0219 (14)	−0.0040 (14)
C17	0.0499 (18)	0.0554 (18)	0.088 (2)	−0.0055 (14)	0.0312 (17)	−0.0082 (17)
C18	0.0405 (16)	0.0505 (17)	0.090 (2)	0.0020 (13)	0.0154 (16)	0.0084 (17)
C19	0.0377 (15)	0.0429 (15)	0.0629 (18)	−0.0022 (12)	0.0048 (13)	0.0132 (13)
C20	0.0377 (15)	0.081 (2)	0.071 (2)	−0.0042 (15)	−0.0059 (15)	0.0233 (18)
C21	0.0509 (18)	0.111 (3)	0.0481 (17)	−0.0082 (18)	−0.0077 (14)	0.0119 (17)
C22	0.0441 (16)	0.097 (2)	0.0409 (15)	−0.0002 (16)	−0.0024 (12)	0.0060 (15)
C23	0.0348 (13)	0.0386 (13)	0.0460 (15)	−0.0035 (11)	0.0049 (11)	0.0078 (12)
C24	0.0407 (14)	0.0377 (14)	0.0478 (15)	−0.0087 (11)	0.0091 (12)	0.0048 (12)
C31	0.0397 (14)	0.0364 (14)	0.0448 (15)	0.0083 (11)	−0.0041 (11)	−0.0010 (12)
C32	0.0597 (17)	0.0554 (16)	0.0327 (13)	−0.0073 (14)	0.0063 (12)	−0.0067 (12)
C33	0.0470 (16)	0.0560 (17)	0.0355 (15)	−0.0037 (13)	0.0093 (12)	−0.0030 (13)

Geometric parameters (Å, º)

Mn—O1	2.0574 (16)	C3—C4	1.402 (4)
Mn—O5	2.1991 (17)	C3—H3	0.9300
Mn—N1	2.2487 (19)	C4—C12	1.407 (3)
Mn—N2	2.357 (2)	C4—C5	1.421 (4)
Mn—N3	2.285 (2)	C5—C6	1.338 (4)
Mn—N4	2.263 (2)	C5—H5	0.9300
BrA—C33	1.910 (4)	C6—C7	1.433 (4)
BrB—C33	1.922 (5)	C6—H6	0.9300
C31—C32	1.493 (4)	C7—C8	1.393 (4)
C32—C33	1.307 (4)	C7—C11	1.404 (3)
C32—H32	0.9300	C8—C9	1.357 (5)
C33—C34A	1.548 (10)	C8—H8	0.9300
C33—C34B	1.41 (3)	C9—C10	1.404 (4)
C34A—O3A	1.183 (14)	C9—H9	0.9300
C34A—O4A	1.285 (14)	C10—H10	0.9300
C34B—O3B	1.26 (3)	C11—C12	1.432 (3)
C34B—O4B	1.25 (2)	C13—C14	1.400 (4)
N1—C1	1.326 (3)	C13—H13	0.9300
N1—C12	1.358 (3)	C14—C15	1.353 (5)
N2—C10	1.322 (3)	C14—H14	0.9300
N2—C11	1.364 (3)	C15—C16	1.404 (4)
N3—C13	1.327 (3)	C15—H15	0.9300
N3—C24	1.354 (3)	C16—C24	1.411 (3)
N4—C22	1.320 (3)	C16—C17	1.428 (4)
N4—C23	1.361 (3)	C17—C18	1.334 (4)
O1—C31	1.262 (3)	C17—H17	0.9300
O2—C31	1.230 (3)	C18—C19	1.430 (4)
O5—H51	0.836	C18—H18	0.9300
O5—H52	0.891	C19—C20	1.401 (4)
O6A—H61	0.930	C19—C23	1.402 (3)
O6A—H62	0.914	C20—C21	1.361 (4)
O6B—H61	0.988	C20—H20	0.9300
O6B—H62	0.953	C21—C22	1.398 (4)
C1—C2	1.390 (4)	C21—H21	0.9300
C1—H1	0.9300	C22—H22	0.9300
C2—C3	1.340 (4)	C23—C24	1.432 (3)
C2—H2	0.9300
O1—Mn—O5	83.11 (6)	C7—C8—H8	119.8
O1—Mn—N1	95.12 (7)	C8—C9—C10	119.0 (3)
O5—Mn—N1	92.98 (7)	C8—C9—H9	120.5
O1—Mn—N4	101.55 (7)	C10—C9—H9	120.5
O5—Mn—N4	104.21 (7)	N2—C10—C9	122.7 (3)
N1—Mn—N4	157.26 (7)	N2—C10—H10	118.6
O1—Mn—N3	162.18 (8)	C9—C10—H10	118.6
O5—Mn—N3	81.91 (7)	N2—C11—C7	122.9 (2)
N1—Mn—N3	95.25 (7)	N2—C11—C12	118.1 (2)
N4—Mn—N3	73.02 (7)	C7—C11—C12	118.9 (2)
O1—Mn—N2	109.18 (7)	N1—C12—C4	121.8 (2)
O5—Mn—N2	161.13 (7)	N1—C12—C11	118.0 (2)
N1—Mn—N2	72.15 (7)	C4—C12—C11	120.1 (2)
N4—Mn—N2	87.69 (8)	N3—C13—C14	122.9 (3)
N3—Mn—N2	87.82 (7)	N3—C13—H13	118.6
O3A—C34A—O4A	126.9 (10)	C14—C13—H13	118.6
O3A—C34A—C33	121.3 (10)	C15—C14—C13	119.3 (3)
O4A—C34A—C33	111.8 (7)	C15—C14—H14	120.3
O4B—C34B—O3B	120 (2)	C13—C14—H14	120.3
O4B—C34B—C33	120 (2)	C14—C15—C16	119.9 (3)
O3B—C34B—C33	120.0 (16)	C14—C15—H15	120.0
C1—N1—C12	118.0 (2)	C16—C15—H15	120.0
C1—N1—Mn	124.22 (17)	C15—C16—C24	117.2 (3)
C12—N1—Mn	117.78 (16)	C15—C16—C17	123.1 (3)
C10—N2—C11	117.9 (2)	C24—C16—C17	119.7 (3)
C10—N2—Mn	128.3 (2)	C18—C17—C16	120.6 (3)
C11—N2—Mn	113.75 (15)	C18—C17—H17	119.7
C13—N3—C24	118.1 (2)	C16—C17—H17	119.7
C13—N3—Mn	126.59 (19)	C17—C18—C19	121.5 (3)
C24—N3—Mn	115.24 (15)	C17—C18—H18	119.2
C22—N4—C23	118.0 (2)	C19—C18—H18	119.2
C22—N4—Mn	126.25 (17)	C20—C19—C23	117.2 (2)
C23—N4—Mn	115.78 (15)	C20—C19—C18	123.2 (3)
C31—O1—Mn	143.31 (17)	C23—C19—C18	119.5 (3)
Mn—O5—H51	117.39	C21—C20—C19	119.8 (2)
Mn—O5—H52	131.62	C21—C20—H20	120.1
H51—O5—H52	102.85	C19—C20—H20	120.1
H61—O6A—H62	98.6	C20—C21—C22	119.3 (3)
H61—O6B—H62	92.2	C20—C21—H21	120.4
N1—C1—C2	123.1 (2)	C22—C21—H21	120.4
N1—C1—H1	118.4	N4—C22—C21	122.9 (3)
C2—C1—H1	118.4	N4—C22—H22	118.5
C3—C2—C1	119.5 (3)	C21—C22—H22	118.5
C3—C2—H2	120.2	N4—C23—C19	122.8 (2)
C1—C2—H2	120.2	N4—C23—C24	117.9 (2)
C2—C3—C4	119.8 (2)	C19—C23—C24	119.3 (2)
C2—C3—H3	120.1	N3—C24—C16	122.6 (2)
C4—C3—H3	120.1	N3—C24—C23	118.0 (2)
C3—C4—C12	117.7 (2)	C16—C24—C23	119.4 (2)
C3—C4—C5	123.1 (3)	O2—C31—O1	126.1 (2)
C12—C4—C5	119.2 (3)	O2—C31—C32	116.6 (2)
C6—C5—C4	121.0 (3)	O1—C31—C32	117.3 (2)
C6—C5—H5	119.5	C33—C32—C31	125.1 (2)
C4—C5—H5	119.5	C33—C32—H32	117.5
C5—C6—C7	121.4 (3)	C31—C32—H32	117.5
C5—C6—H6	119.3	C32—C33—C34B	125.0 (8)
C7—C6—H6	119.3	C32—C33—C34A	129.4 (5)
C8—C7—C11	117.0 (3)	C32—C33—BrA	119.3 (2)
C8—C7—C6	123.6 (3)	C34A—C33—BrA	111.2 (4)
C11—C7—C6	119.3 (3)	C32—C33—BrB	117.6 (3)
C9—C8—C7	120.4 (3)	C34B—C33—BrB	117.3 (8)
C9—C8—H8	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4A	0.84	1.93	2.747 (5)	166
O5—H51···O4B	0.84	2.03	2.849 (9)	165
O5—H52···O3A^i	0.89	1.92	2.796 (5)	167
O5—H52···O4B^i	0.89	2.05	2.854 (8)	149
O6A—H61···O2	0.93	1.92	2.706 (5)	141
O6A—H62···O4A^ii	0.91	2.09	2.909 (6)	148
O6B—H61···O2	0.99	1.92	2.736 (10)	138
O6B—H62···O4A^ii	0.95	2.09	2.851 (10)	136

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+3/2.