A new one-dimensional coordination polymer of 5-(1,3-dioxo-4,5,6,7-tetra­phenyl­isoindolin-2-yl)isophthalic acid with manganese

The coordination polymer catena-poly[[(di­methyl­formamide-κO)[μ₃-5-(1,3-di­oxo-4,5,6,7-tetra­phenyl­isoindolin-2-yl)isophthalato-κ⁴O¹,O^1′:O³:O^3′](methanol-κO)man­gan­ese(III)] di­methyl­formamide monosolvate], {[Mn(C₄₀H₂₃NO₆)(CH₃OH)(C₃H₇NO)]·C₃H₇NO}_n, has been synthesized from the reaction of 5-(1,3-dioxo-4,5,6,7-tetra­phenyl­isoindolin-2-yl)isophthalic acid and man­gan­ese(II) acetate tetra­hydrate in a glass tube at room temperature by solvent diffusion. The Mn^II centre is hexa­coordinated by two O atoms from one chelating carboxyl­ate group, by two O atoms from two monodentate carboxyl­ate groups and by one O atom each from a methanol and a di­methyl­formamide (DMF) ligand. The single-crystal structure crystallizes in the triclinic space group P. Moreover, the coordination polymer shows one-dimensional 2-connected {0} uninodal chain networks, and free DMF mol­ecules are connected to the chains by O—H...O hydrogen bonds. The thermogravimetric and photoluminescent properties of the compound have also been investigated.

S1. Introduction

In recent years, coordination polymers (CPs) have attracted much attention as a large family of functional materials. Up to now, the applications of coordination polymers ranged across many areas, such as heterogeneous catalysis, sensing, gas storage, imaging and drug delivery (Park et al., 2006; Zheng et al., 2013; Lee et al., 2007; Liu et al., 2011; Gao et al., 2013). In contrast to pure organic or inorganic materials, the wide choices of metal ions and organic ligands afford coordination polymers with different morphologies and physicochemical properties, and consequently they have the potential to show promise for use in diverse applications (Della Rocca et al., 2011). Therefore, the design and synthesis of novel CPs with functional ligands have been of great inter­est.

We designed and synthesized the rigid organic ligand 5-(1,3-dioxo-4,5,6,7-tetra­phenyl­isoindolin- 2-yl)isophthalic acid (H₂L), which contains four phenyl rings connected to a central aromatic ring, which is likely to enhance the electronic conjugation effect and may lead to the ligand having potential fluorescence properties. Furthermore, the conformation of the four phenyl substituents can increase the structural diversity of its coordination complexes. By means of liquid phase diffusion, self-assembly between H₂L and the corresponding metal salt leads to the new complex {[Mn(L)(DMF)(MeOH)].DMF}_n, (I).

S2. Experimental

All reagents and solvents were purchased from commercial sources and were used without further purification. IR spectra were recorded on a TENSOR 27 spectrometer by using KBr pellets in the range 4000–400 cm^-1. Thermogravimetric analysis (TGA) was performed under an air atmosphere with a heating rate of 5 K min^-1 on a Q600 Thermal analyzer. CHN elemental analyses were performed on an Elementar Vario EL analyzer. All fluorescence measurements were conducted on an F-280 spectrofluorimeter equipped with a xenon lamp source, and the scan speed was set at 240 nm min^-1. The ¹H NMR measurements were conducted on a Bruker AV 40.

S2.1. \ Synthesis and crystallization of 5-(1,3-dioxo-4,5,6,7-tetra­phenyl­isoindolin-2-yl)isophthalic acid (H₂L)

5-Amino­isophthalic acid (0.324 g, 1.5 mmol) and tetra­phenyl­phthalic anhydride (0.686 g, 1.5 mmol) were dissolved in anhydrous N,N-di­methyl-formamide (DMF, 6 ml). The solution was heated at reflux for 13 h and then allowed to cool to room temperature. The mixture was poured into water (50 ml). A pale-yellow precipitate formed which was filtered off and washed with H₂O (4 × 20 ml) and dried under vacuum (yield: 0.76 g, 81%). ¹H NMR (DMSO-d₆): 13.45 (s, 2H), 8.44 (t, 1H), 8.18 (d, 2H), 7.2 (m, 10H), 6.9 (m, 10H). Analysis calculated (%) for C₄₀H₂₅NO₆: C 78.10, H 4.10, N 2.27; found: C 78.06, H 4.20, N 2.42.

S2.2. \ Synthesis and crystallization of {[Mn(L)(DMF)(MeOH) ].DMF}_{n, (I)}

A DMF (5 ml) solution of manganese(II) acetate tetra­hydrate (0.025 g, 0.1 mmol) was placed at the bottom of a glass tube. A DMF–MeOH solution (5 ml, 1:1 v/v) and an MeOH (5 ml) solution of H₂L (0.030 g, 0.05 mmol) were placed in the middle and upper layers of the glass tube, respectively. By slow diffusion of the above rea­cta­nts at room temperature for several days, some pale-yellow crystals were produced (yield: 45%, based on Mn). Analysis calculated (%) for C₄₇H₄₁MnN₃O₉: C 66.66, H 4.88, N 4.96; found: C 66.76, H 4.60, N 4.92.

S2.3. IR spectroscopic data

H₂L: FT–IR (KBr pellet, ν, cm^-1): 3442 (s, ν_O—H), 1776 (m), 1723 (vs, ν_C═O asymmetric of pyromellitic di­imide), 1644 (s, ν_C═O asymmetric of carb­oxy­lic acid), 1597 (vw), 1494 (w), 1442 (m, ν_C═C of aromatic ring), 1362 (s, ν_C—N), 1266 (m, ν_C—O), 1174 (m), 1111 (m), 764 (m), 698 (s), 672 (w), 633 (w), 563 (w), 532 (vw).

Coordination polymer (I): FT–IR (KBr pellet, ν, cm^-1): 3443 (s), 1771 (m), 1714 (vs), 1650 (vs), 1616 (s), 1572 (vs), 1495 (w), 1443 (m), 1411 (s), 1368 (vs), 1213 (w), 1120 (m), 1026 (m), 911 (vw), 766 (m), 698 (m), 563 (w), 526 (w).

S2.4. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms bonded to C atoms and hy­droxy O atoms were placed at calculated positions and refined using a riding-model approximation, with C—H = 0.95 Å and U_iso(H) = 1.5U_eq(C) and O—H = 0.9337 Å and U_iso(H) = 1.5U_eq(O). The H atomson the methanol O atom was located in a difference Fourier map and treated as riding, with O—H = 0.9337 Å and U_iso(H) = 1.5U_eq(O).

S3. Results and discussion

The general features of the FT–IR spectra for compound (I) are almost identical through the region from 4000 to 500 cm^-1 (Prasad et al., 2010). Absorptions at 1770–1780 and 1710–1730cm^-1 correspond to the C═ O stretching-frequency asymmetric and symmetric vibrations of pyromellitic di­imide. The absorption at 1370 cm^-1 is attributed to the stretching vibration of the C—N—C moiety (Fang et al., 2014). The characteristic strongb bands of coordinated carboxyl­ate groups are shown in the 1650 cm^-1 for the C═O asymmetric stretching of a carboxyl­ate group. The bands in the regions 1607–1620 and 1448–1469 cm^-1 and at 1400 cm^-1 belong to the C═C stretching frequency of aromatic rings. The absorption at 1572 cm^-1 is attributed to a carboxyl­ate group connected to a metal ion (Karmakar & Goldberg, 2011).

Compound (I) crystallizes in the triclinic space group P1, with the asymmetric unit consisting of one Mn^II centre, one 5-(1,3-dioxo-4,5,6,7-tetra­phenyl­isoindolin-2-yl)isophthalate (L^2-) ligand, coordinated methanol and DMF ligands and one free DMF solvent molecule. All atoms are located on general positions. As shown in Fig. 1, the Mn^II centre is hexacoordinated by two O atoms from one chelating carboxyl­ate group, two O atoms from two monodentate carboxyl­ate groups, and two O atoms from methanol and DMF ligands. The Mn—O bond lengths are in the range 2.1145 (16)–2.3685 (16) Å (Table 2), and the bond angles around the Mn^II atom vary from 57.52 (6) to 178.70 (8)°. The Mn···Mn separation is 4.4102 (7) Å. These values are comparable to those in reported Mn compounds (Jia et al., 2014).

Compound (I) is constructed from binuclear metal clusters and L^2- ligands as secondary building units. As shown in Fig. 2, each L^2- ligand coordinates to two Mn₂ units, while each Mn₂ unit connects four L^2- ligands. Thus, compound (I) displays a 2-connected {0} uninodal chain network. In this connected chains, there are O—H···O hydrogen-bonding inter­actions [O9···O8 = 2.617 (3) Å], so that free DMF molecules are connected to the chains (Fig. 2 and Table 3).

Thermogravimetric analyses (TGA) were carried out under air from room temperature to about 773.15 K, with a heating rate of 5 K min^-1. The TGA results indicate that the compound (I) is stable up to 633.15 K, after which the framework starts to collapse as the organic ligands decompose. To study the photoluminescent properties of compound (I), its emission spectrum has been investigated at room temperature. As depicted in Fig. 3, H₂L shows a broad emission and a main peak at 468 nm upon excitation at 420 nm, which should be attributed to π* → π and/or π* → n transitions (Xue et al., 2008). The six aromatic rings in the molecule of H₂L suggest it may have luminescence properties, which is consistent with the properties of extended polycyclic arenes (Bock et al., 2014). Compared to H₂L, compound (I) reveals a blue-shift by 3 nm to 465 nm, with an excitation band at 426 nm, which indicates the mechanism should be a ligand-centred emission (Li et al., 2009). This slight blue-shift in compound (I) may due to the increased energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of deprotonated L^2- by metal [not clear] ions (Cui et al., 2012).

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXL (Sheldrick, 2008); software used to prepare material for publication: APEX2 (Bruker, 2014).

Figures

	Fig. 1. The coordination environment of the Mn^II centre in (I), showing a partial atom-labelling scheme and 30% probability displacement ellipsoids. H atoms have been omitted for clarity. [Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+2; (iii) x+1, y, z.] [Please provide revision]
	Fig. 2. A view of the one-dimensional chain of (I). Hydrogen bonds are drawn as green dashed lines. The coordinated DMF molecules and H atoms have been omitted for clarity.
	Fig. 3. The solid-state emission spectra of ligand H2L and coordination polymer (I) at room temperature.

catena-Poly[[(dimethylformamide-κO)[µ₃-5-(1,3-dioxo-4,5,6,7-tetraphenylisoindolin-2-yl)isophthalato-κ⁴O¹,O^1':O³:O^3'](methanol-κO)manganese(III)] dimethylformamide monosolvate]

Crystal data

[Mn(C40H23NO6)(CH4O)(C3H7NO)]·C3H7NO	V = 2097.8 (2) Å^3
Mr = 846.77	Z = 2
Triclinic, P1	F(000) = 882
Hall symbol: -P 1	Dx = 1.341 Mg m^−3
a = 10.3336 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.3984 (10) Å	θ = 2.3–25.0°
c = 15.2649 (8) Å	µ = 0.38 mm^−1
α = 90.673 (5)°	T = 173 K
β = 98.120 (4)°	Prism, pink
γ = 110.761 (5)°	0.22 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer	7389 independent reflections
Radiation source: fine-focus sealed tube	5223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scan	θmax = 25.0°, θmin = 2.3°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −12→11
Tmin = 0.935, Tmax = 0.970	k = −16→17
14942 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.070P] where P = (Fo^2 + 2Fc^2)/3
7389 reflections	(Δ/σ)max = 0.001
547 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.34 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
C1	0.1812 (2)	0.42880 (17)	0.38770 (16)	0.0280 (6)
C2	0.2430 (2)	0.45821 (18)	0.47640 (16)	0.0295 (6)
C3	0.2575 (2)	0.55645 (18)	0.50517 (16)	0.0295 (6)
C4	0.2150 (2)	0.61977 (18)	0.44780 (16)	0.0315 (6)
C5	0.1557 (2)	0.58829 (18)	0.35810 (16)	0.0305 (6)
C6	0.1379 (2)	0.49097 (18)	0.33217 (16)	0.0294 (6)
C7	0.0684 (2)	0.43477 (19)	0.24478 (18)	0.0343 (6)
C8	0.1540 (2)	0.33317 (19)	0.33483 (17)	0.0321 (6)
C9	0.1132 (3)	0.65298 (18)	0.29307 (17)	0.0362 (6)
C10	0.1763 (3)	0.6769 (2)	0.2184 (2)	0.0553 (8)
H10	0.2526	0.6570	0.2106	0.066*
C11	0.1286 (4)	0.7299 (3)	0.1548 (2)	0.0726 (10)
H11	0.1730	0.7467	0.1038	0.087*
C12	0.0181 (4)	0.7585 (3)	0.1648 (2)	0.0717 (10)
H12	−0.0159	0.7931	0.1200	0.086*
C13	−0.0429 (3)	0.7369 (2)	0.2397 (2)	0.0614 (9)
H13	−0.1185	0.7575	0.2475	0.074*
C14	0.0051 (3)	0.6854 (2)	0.3038 (2)	0.0450 (7)
H14	−0.0366	0.6719	0.3561	0.054*
C15	0.2338 (2)	0.72254 (19)	0.48178 (17)	0.0364 (6)
C16	0.3170 (3)	0.8053 (2)	0.4445 (2)	0.0497 (8)
H16	0.3607	0.7970	0.3958	0.060*
C17	0.3372 (3)	0.8999 (2)	0.4774 (2)	0.0671 (10)
H17	0.3946	0.9563	0.4513	0.081*
C18	0.2739 (4)	0.9128 (3)	0.5484 (3)	0.0723 (11)
H18	0.2889	0.9780	0.5716	0.087*
C19	0.1900 (3)	0.8316 (3)	0.5850 (2)	0.0616 (9)
H19	0.1456	0.8402	0.6333	0.074*
C20	0.1696 (3)	0.7372 (2)	0.55206 (19)	0.0452 (7)
H20	0.1106	0.6812	0.5778	0.054*
C21	0.3198 (2)	0.59491 (18)	0.59910 (16)	0.0328 (6)
C22	0.4483 (3)	0.6727 (2)	0.61892 (19)	0.0442 (7)
H22	0.4999	0.7004	0.5727	0.053*
C23	0.5009 (3)	0.7097 (2)	0.7056 (2)	0.0580 (9)
H23	0.5889	0.7627	0.7187	0.070*
C24	0.4278 (3)	0.6708 (3)	0.7728 (2)	0.0655 (10)
H24	0.4642	0.6975	0.8321	0.079*
C25	0.3019 (3)	0.5932 (3)	0.75458 (19)	0.0620 (9)
H25	0.2515	0.5655	0.8013	0.074*
C26	0.2486 (3)	0.5554 (2)	0.66821 (18)	0.0444 (7)
H26	0.1616	0.5013	0.6560	0.053*
C27	0.2915 (2)	0.39208 (18)	0.53592 (16)	0.0323 (6)
C28	0.4247 (3)	0.4253 (2)	0.58625 (17)	0.0414 (7)
H28	0.4864	0.4917	0.5825	0.050*
C29	0.4684 (3)	0.3637 (3)	0.6413 (2)	0.0547 (8)
H29	0.5599	0.3878	0.6749	0.066*
C30	0.3815 (4)	0.2679 (3)	0.6483 (2)	0.0644 (9)
H30	0.4116	0.2259	0.6870	0.077*
C31	0.2507 (3)	0.2334 (2)	0.5989 (2)	0.0570 (8)
H31	0.1903	0.1667	0.6029	0.068*
C32	0.2056 (3)	0.2947 (2)	0.54328 (18)	0.0414 (7)
H32	0.1143	0.2695	0.5096	0.050*
C33	0.0371 (2)	0.26727 (18)	0.18019 (16)	0.0305 (6)
C34	−0.1031 (2)	0.22500 (18)	0.14403 (16)	0.0320 (6)
H34	−0.1709	0.2438	0.1679	0.038*
C35	−0.1440 (2)	0.15485 (17)	0.07257 (15)	0.0280 (6)
C36	−0.0431 (2)	0.12884 (17)	0.03781 (15)	0.0276 (5)
H36	−0.0708	0.0799	−0.0103	0.033*
C37	0.0976 (2)	0.17370 (17)	0.07278 (15)	0.0277 (6)
C38	0.1373 (2)	0.24164 (17)	0.14548 (16)	0.0305 (6)
H38	0.2331	0.2705	0.1714	0.037*
C39	0.2107 (2)	0.15265 (18)	0.03247 (17)	0.0328 (6)
C40	−0.2964 (2)	0.10917 (19)	0.03119 (16)	0.0323 (6)
C41	−0.4282 (6)	0.4761 (4)	−0.1133 (3)	0.1265 (17)
H41A	−0.3774	0.4970	−0.1635	0.190*
H41B	−0.4460	0.5326	−0.0881	0.190*
H41C	−0.5175	0.4219	−0.1336	0.190*
C42	−0.2125 (5)	0.5149 (3)	−0.0003 (3)	0.1153 (17)
H42A	−0.1613	0.4807	0.0375	0.173*
H42B	−0.2324	0.5631	0.0364	0.173*
H42C	−0.1554	0.5499	−0.0443	0.173*
C43	−0.3851 (4)	0.3475 (3)	−0.0270 (3)	0.0763 (11)
H43	−0.3265	0.3289	0.0175	0.092*
H9	−0.6942	0.0447	−0.1913	0.104 (13)*
C44	0.0833 (4)	0.0247 (3)	0.3879 (2)	0.0824 (11)
H44A	−0.0012	0.0328	0.4031	0.124*
H44B	0.1649	0.0848	0.4085	0.124*
H44C	0.0960	−0.0327	0.4165	0.124*
C45	0.1913 (4)	0.0118 (3)	0.2553 (3)	0.0964 (14)
H45A	0.1710	0.0105	0.1906	0.145*
H45B	0.2160	−0.0459	0.2723	0.145*
H45C	0.2699	0.0731	0.2777	0.145*
C46	−0.0539 (4)	−0.0119 (2)	0.2437 (2)	0.0569 (8)
H46	−0.0589	−0.0214	0.1814	0.068*
C47	−0.5165 (4)	0.0373 (4)	−0.2054 (2)	0.1001 (15)
H47A	−0.4258	0.0512	−0.1677	0.150*
H47B	−0.5021	0.0722	−0.2600	0.150*
H47C	−0.5612	−0.0345	−0.2203	0.150*
Mn1	−0.58074 (3)	0.12182 (3)	−0.02265 (3)	0.03688 (14)
N1	0.08109 (19)	0.34133 (15)	0.25275 (13)	0.0325 (5)
N2	−0.3446 (3)	0.4419 (2)	−0.0459 (2)	0.0818 (9)
N3	0.0691 (3)	0.00866 (18)	0.29286 (18)	0.0579 (7)
O1	0.18705 (19)	0.26302 (14)	0.35369 (12)	0.0471 (5)
O2	0.0113 (2)	0.45931 (14)	0.17947 (13)	0.0501 (5)
O3	−0.37364 (15)	0.15721 (13)	0.04385 (13)	0.0479 (5)
O4	−0.33606 (15)	0.02934 (13)	−0.01469 (12)	0.0414 (5)
O5	0.18580 (16)	0.11786 (13)	−0.04591 (12)	0.0411 (5)
O6	0.32789 (16)	0.17261 (14)	0.08006 (12)	0.0472 (5)
O7	−0.4975 (2)	0.27984 (18)	−0.06437 (17)	0.0812 (7)
O8	−0.1625 (2)	−0.01978 (18)	0.27139 (14)	0.0717 (7)
O9	−0.6035 (2)	0.07047 (18)	−0.15961 (13)	0.0672 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0258 (12)	0.0296 (14)	0.0282 (14)	0.0102 (10)	0.0027 (10)	−0.0042 (12)
C2	0.0263 (12)	0.0312 (14)	0.0290 (14)	0.0081 (10)	0.0036 (10)	−0.0030 (12)
C3	0.0262 (12)	0.0315 (15)	0.0276 (14)	0.0073 (10)	0.0024 (10)	−0.0033 (12)
C4	0.0300 (12)	0.0298 (14)	0.0321 (15)	0.0078 (10)	0.0046 (11)	−0.0056 (12)
C5	0.0304 (12)	0.0315 (15)	0.0307 (15)	0.0127 (10)	0.0047 (11)	−0.0010 (12)
C6	0.0291 (12)	0.0348 (15)	0.0245 (14)	0.0130 (10)	0.0011 (10)	−0.0040 (12)
C7	0.0314 (13)	0.0394 (16)	0.0329 (16)	0.0156 (11)	0.0007 (12)	−0.0050 (13)
C8	0.0288 (12)	0.0369 (16)	0.0313 (15)	0.0137 (11)	0.0027 (11)	−0.0037 (12)
C9	0.0403 (14)	0.0312 (15)	0.0353 (16)	0.0123 (11)	0.0026 (12)	−0.0030 (12)
C10	0.0662 (19)	0.065 (2)	0.048 (2)	0.0356 (16)	0.0188 (16)	0.0125 (17)
C11	0.104 (3)	0.083 (3)	0.049 (2)	0.050 (2)	0.027 (2)	0.030 (2)
C12	0.096 (3)	0.073 (2)	0.060 (2)	0.048 (2)	0.007 (2)	0.027 (2)
C13	0.067 (2)	0.063 (2)	0.068 (2)	0.0399 (17)	0.0112 (18)	0.0160 (19)
C14	0.0498 (16)	0.0427 (17)	0.0464 (18)	0.0203 (13)	0.0101 (14)	0.0065 (14)
C15	0.0368 (14)	0.0331 (15)	0.0358 (16)	0.0127 (11)	−0.0053 (12)	−0.0052 (13)
C16	0.0503 (16)	0.0368 (18)	0.056 (2)	0.0110 (13)	0.0011 (14)	−0.0014 (15)
C17	0.067 (2)	0.0351 (19)	0.080 (3)	0.0049 (15)	−0.0164 (19)	−0.0017 (18)
C18	0.086 (2)	0.046 (2)	0.079 (3)	0.0329 (19)	−0.029 (2)	−0.029 (2)
C19	0.071 (2)	0.065 (2)	0.055 (2)	0.0421 (18)	−0.0106 (17)	−0.0245 (19)
C20	0.0442 (15)	0.0467 (18)	0.0454 (18)	0.0208 (13)	−0.0015 (13)	−0.0105 (14)
C21	0.0300 (13)	0.0360 (15)	0.0303 (15)	0.0118 (11)	−0.0011 (11)	−0.0070 (12)
C22	0.0343 (14)	0.0458 (17)	0.0446 (18)	0.0080 (12)	−0.0012 (12)	−0.0048 (14)
C23	0.0452 (16)	0.054 (2)	0.056 (2)	0.0046 (14)	−0.0165 (16)	−0.0162 (17)
C24	0.066 (2)	0.082 (3)	0.0372 (19)	0.0219 (18)	−0.0160 (16)	−0.0257 (18)
C25	0.063 (2)	0.087 (3)	0.0307 (18)	0.0214 (18)	0.0060 (15)	−0.0059 (17)
C26	0.0367 (14)	0.0503 (18)	0.0375 (17)	0.0065 (12)	0.0032 (13)	−0.0064 (14)
C27	0.0356 (13)	0.0368 (16)	0.0270 (14)	0.0160 (12)	0.0051 (11)	−0.0002 (12)
C28	0.0381 (14)	0.0527 (18)	0.0354 (16)	0.0197 (13)	0.0029 (12)	0.0027 (14)
C29	0.0478 (17)	0.081 (3)	0.0430 (19)	0.0352 (17)	0.0002 (14)	0.0087 (18)
C30	0.076 (2)	0.073 (3)	0.062 (2)	0.046 (2)	0.0151 (19)	0.027 (2)
C31	0.069 (2)	0.0454 (19)	0.061 (2)	0.0227 (16)	0.0175 (18)	0.0149 (17)
C32	0.0447 (15)	0.0403 (17)	0.0383 (17)	0.0147 (13)	0.0048 (13)	−0.0011 (14)
C33	0.0296 (12)	0.0334 (15)	0.0266 (14)	0.0119 (10)	−0.0022 (10)	−0.0098 (11)
C34	0.0270 (12)	0.0373 (15)	0.0340 (15)	0.0148 (11)	0.0042 (11)	−0.0038 (12)
C35	0.0246 (11)	0.0297 (14)	0.0286 (14)	0.0105 (10)	−0.0010 (10)	−0.0016 (11)
C36	0.0287 (12)	0.0276 (14)	0.0266 (14)	0.0122 (10)	−0.0009 (10)	−0.0046 (11)
C37	0.0261 (12)	0.0278 (14)	0.0302 (14)	0.0123 (10)	0.0011 (10)	−0.0024 (11)
C38	0.0223 (11)	0.0345 (15)	0.0315 (14)	0.0101 (10)	−0.0050 (10)	−0.0060 (12)
C39	0.0291 (13)	0.0301 (14)	0.0399 (17)	0.0128 (10)	0.0025 (12)	−0.0074 (12)
C40	0.0251 (12)	0.0361 (16)	0.0328 (15)	0.0090 (11)	0.0006 (11)	−0.0017 (13)
C41	0.164 (5)	0.112 (4)	0.106 (4)	0.061 (4)	−0.002 (4)	0.025 (3)
C42	0.128 (4)	0.083 (3)	0.099 (4)	−0.005 (3)	0.016 (3)	0.001 (3)
C43	0.089 (3)	0.068 (3)	0.077 (3)	0.028 (2)	0.027 (2)	0.017 (2)
C44	0.088 (3)	0.081 (3)	0.066 (3)	0.032 (2)	−0.029 (2)	−0.005 (2)
C45	0.065 (2)	0.096 (3)	0.121 (4)	0.018 (2)	0.020 (2)	0.015 (3)
C46	0.073 (2)	0.053 (2)	0.0404 (19)	0.0244 (17)	−0.0085 (17)	−0.0015 (16)
C47	0.088 (3)	0.189 (5)	0.048 (2)	0.080 (3)	0.010 (2)	−0.012 (3)
Mn1	0.0253 (2)	0.0441 (3)	0.0413 (3)	0.01468 (17)	0.00087 (17)	−0.0110 (2)
N1	0.0328 (10)	0.0340 (13)	0.0305 (12)	0.0162 (9)	−0.0056 (9)	−0.0091 (10)
N2	0.106 (2)	0.060 (2)	0.075 (2)	0.0210 (19)	0.025 (2)	0.0152 (18)
N3	0.0600 (16)	0.0473 (16)	0.0619 (19)	0.0190 (12)	−0.0040 (14)	0.0054 (14)
O1	0.0644 (12)	0.0431 (12)	0.0405 (12)	0.0321 (10)	−0.0030 (9)	−0.0059 (9)
O2	0.0646 (12)	0.0518 (13)	0.0349 (12)	0.0310 (10)	−0.0147 (10)	−0.0076 (10)
O3	0.0230 (9)	0.0464 (12)	0.0722 (14)	0.0157 (8)	−0.0057 (9)	−0.0159 (10)
O4	0.0288 (9)	0.0406 (11)	0.0478 (12)	0.0083 (8)	−0.0046 (8)	−0.0147 (10)
O5	0.0382 (9)	0.0550 (12)	0.0345 (11)	0.0243 (8)	0.0007 (8)	−0.0114 (9)
O6	0.0272 (9)	0.0648 (13)	0.0489 (12)	0.0218 (8)	−0.0074 (8)	−0.0269 (10)
O7	0.0730 (16)	0.0705 (17)	0.092 (2)	0.0183 (13)	0.0081 (14)	0.0140 (15)
O8	0.0635 (14)	0.0978 (19)	0.0546 (15)	0.0368 (13)	−0.0074 (11)	−0.0109 (13)
O9	0.0491 (12)	0.1113 (19)	0.0469 (13)	0.0392 (12)	0.0006 (10)	−0.0177 (13)

Geometric parameters (Å, º)

C1—C6	1.384 (3)	C31—C32	1.384 (4)
C1—C2	1.404 (3)	C31—H31	0.9500
C1—C8	1.504 (3)	C32—H32	0.9500
C2—C3	1.426 (3)	C33—C38	1.382 (3)
C2—C27	1.488 (4)	C33—C34	1.384 (3)
C3—C4	1.409 (3)	C33—N1	1.434 (3)
C3—C21	1.498 (3)	C34—C35	1.389 (3)
C4—C5	1.417 (3)	C34—H34	0.9500
C4—C15	1.499 (3)	C35—C36	1.392 (3)
C5—C6	1.392 (3)	C35—C40	1.512 (3)
C5—C9	1.495 (4)	C36—C37	1.386 (3)
C6—C7	1.497 (3)	C36—H36	0.9500
C7—O2	1.207 (3)	C37—C38	1.385 (3)
C7—N1	1.402 (3)	C37—C39	1.512 (3)
C8—O1	1.201 (3)	C38—H38	0.9500
C8—N1	1.397 (3)	C39—O5	1.247 (3)
C9—C10	1.380 (4)	C39—O6	1.256 (3)
C9—C14	1.382 (4)	C39—Mn1^i	2.595 (2)
C10—C11	1.384 (4)	C40—O4	1.243 (3)
C10—H10	0.9500	C40—O3	1.259 (3)
C11—C12	1.371 (5)	C41—N2	1.452 (5)
C11—H11	0.9500	C41—H41A	0.9800
C12—C13	1.370 (4)	C41—H41B	0.9800
C12—H12	0.9500	C41—H41C	0.9800
C13—C14	1.377 (4)	C42—N2	1.467 (5)
C13—H13	0.9500	C42—H42A	0.9800
C14—H14	0.9500	C42—H42B	0.9800
C15—C16	1.383 (4)	C42—H42C	0.9800
C15—C20	1.390 (3)	C43—O7	1.274 (4)
C16—C17	1.379 (4)	C43—N2	1.320 (4)
C16—H16	0.9500	C43—H43	0.9500
C17—C18	1.386 (5)	C44—N3	1.445 (4)
C17—H17	0.9500	C44—H44A	0.9800
C18—C19	1.366 (5)	C44—H44B	0.9800
C18—H18	0.9500	C44—H44C	0.9800
C19—C20	1.376 (4)	C45—N3	1.445 (4)
C19—H19	0.9500	C45—H45A	0.9800
C20—H20	0.9500	C45—H45B	0.9800
C21—C26	1.384 (3)	C45—H45C	0.9800
C21—C22	1.390 (3)	C46—O8	1.223 (3)
C22—C23	1.380 (4)	C46—N3	1.314 (4)
C22—H22	0.9500	C46—H46	0.9500
C23—C24	1.368 (4)	C47—O9	1.414 (3)
C23—H23	0.9500	C47—H47A	0.9800
C24—C25	1.370 (4)	C47—H47B	0.9800
C24—H24	0.9500	C47—H47C	0.9800
C25—C26	1.380 (4)	Mn1—O3	2.1145 (16)
C25—H25	0.9500	Mn1—O4^ii	2.1545 (19)
C26—H26	0.9500	Mn1—O9	2.162 (2)
C27—C32	1.384 (3)	Mn1—O6^iii	2.1829 (16)
C27—C28	1.392 (3)	Mn1—O7	2.264 (2)
C28—C29	1.376 (4)	Mn1—O5^iii	2.3685 (16)
C28—H28	0.9500	Mn1—C39^iii	2.595 (2)
C29—C30	1.368 (4)	O4—Mn1^ii	2.1545 (19)
C29—H29	0.9500	O5—Mn1^i	2.3685 (16)
C30—C31	1.366 (4)	O6—Mn1^i	2.1829 (16)
C30—H30	0.9500	O9—H9	0.9339
C6—C1—C2	122.3 (2)	C33—C34—C35	119.6 (2)
C6—C1—C8	108.0 (2)	C33—C34—H34	120.2
C2—C1—C8	129.7 (2)	C35—C34—H34	120.2
C1—C2—C3	115.2 (2)	C34—C35—C36	119.4 (2)
C1—C2—C27	122.4 (2)	C34—C35—C40	120.33 (19)
C3—C2—C27	122.3 (2)	C36—C35—C40	120.2 (2)
C4—C3—C2	122.1 (2)	C37—C36—C35	120.6 (2)
C4—C3—C21	118.2 (2)	C37—C36—H36	119.7
C2—C3—C21	119.8 (2)	C35—C36—H36	119.7
C3—C4—C5	121.1 (2)	C38—C37—C36	119.66 (19)
C3—C4—C15	119.6 (2)	C38—C37—C39	118.43 (19)
C5—C4—C15	119.3 (2)	C36—C37—C39	121.9 (2)
C6—C5—C4	115.9 (2)	C33—C38—C37	119.7 (2)
C6—C5—C9	120.3 (2)	C33—C38—H38	120.1
C4—C5—C9	123.8 (2)	C37—C38—H38	120.1
C1—C6—C5	123.3 (2)	O5—C39—O6	122.6 (2)
C1—C6—C7	108.6 (2)	O5—C39—C37	119.7 (2)
C5—C6—C7	128.0 (2)	O6—C39—C37	117.7 (2)
O2—C7—N1	124.5 (2)	O5—C39—Mn1^i	65.55 (12)
O2—C7—C6	130.4 (2)	O6—C39—Mn1^i	57.05 (11)
N1—C7—C6	105.0 (2)	C37—C39—Mn1^i	174.74 (18)
O1—C8—N1	124.3 (2)	O4—C40—O3	124.5 (2)
O1—C8—C1	130.5 (2)	O4—C40—C35	118.6 (2)
N1—C8—C1	105.2 (2)	O3—C40—C35	116.8 (2)
C10—C9—C14	118.7 (3)	N2—C41—H41A	109.5
C10—C9—C5	120.4 (2)	N2—C41—H41B	109.5
C14—C9—C5	120.9 (2)	H41A—C41—H41B	109.5
C9—C10—C11	120.0 (3)	N2—C41—H41C	109.5
C9—C10—H10	120.0	H41A—C41—H41C	109.5
C11—C10—H10	120.0	H41B—C41—H41C	109.5
C12—C11—C10	120.7 (3)	N2—C42—H42A	109.5
C12—C11—H11	119.6	N2—C42—H42B	109.5
C10—C11—H11	119.6	H42A—C42—H42B	109.5
C13—C12—C11	119.5 (3)	N2—C42—H42C	109.5
C13—C12—H12	120.2	H42A—C42—H42C	109.5
C11—C12—H12	120.2	H42B—C42—H42C	109.5
C12—C13—C14	120.1 (3)	O7—C43—N2	124.3 (4)
C12—C13—H13	119.9	O7—C43—H43	117.8
C14—C13—H13	119.9	N2—C43—H43	117.8
C13—C14—C9	120.9 (3)	N3—C44—H44A	109.5
C13—C14—H14	119.5	N3—C44—H44B	109.5
C9—C14—H14	119.5	H44A—C44—H44B	109.5
C16—C15—C20	118.3 (2)	N3—C44—H44C	109.5
C16—C15—C4	120.7 (2)	H44A—C44—H44C	109.5
C20—C15—C4	121.0 (2)	H44B—C44—H44C	109.5
C17—C16—C15	120.7 (3)	N3—C45—H45A	109.5
C17—C16—H16	119.7	N3—C45—H45B	109.5
C15—C16—H16	119.7	H45A—C45—H45B	109.5
C16—C17—C18	120.1 (3)	N3—C45—H45C	109.5
C16—C17—H17	119.9	H45A—C45—H45C	109.5
C18—C17—H17	119.9	H45B—C45—H45C	109.5
C19—C18—C17	119.7 (3)	O8—C46—N3	125.4 (3)
C19—C18—H18	120.1	O8—C46—H46	117.3
C17—C18—H18	120.1	N3—C46—H46	117.3
C18—C19—C20	120.1 (3)	O9—C47—H47A	109.5
C18—C19—H19	119.9	O9—C47—H47B	109.5
C20—C19—H19	119.9	H47A—C47—H47B	109.5
C19—C20—C15	121.1 (3)	O9—C47—H47C	109.5
C19—C20—H20	119.4	H47A—C47—H47C	109.5
C15—C20—H20	119.4	H47B—C47—H47C	109.5
C26—C21—C22	118.3 (2)	O3—Mn1—O4^ii	97.45 (7)
C26—C21—C3	120.5 (2)	O3—Mn1—O9	111.99 (7)
C22—C21—C3	121.1 (2)	O4^ii—Mn1—O9	90.86 (8)
C23—C22—C21	120.1 (3)	O3—Mn1—O6^iii	99.95 (7)
C23—C22—H22	120.0	O4^ii—Mn1—O6^iii	91.10 (7)
C21—C22—H22	120.0	O9—Mn1—O6^iii	147.45 (7)
C24—C23—C22	120.7 (3)	O3—Mn1—O7	83.79 (8)
C24—C23—H23	119.7	O4^ii—Mn1—O7	178.70 (8)
C22—C23—H23	119.7	O9—Mn1—O7	88.30 (9)
C23—C24—C25	120.0 (3)	O6^iii—Mn1—O7	89.07 (8)
C23—C24—H24	120.0	O3—Mn1—O5^iii	157.22 (6)
C25—C24—H24	120.0	O4^ii—Mn1—O5^iii	87.08 (6)
C24—C25—C26	119.8 (3)	O9—Mn1—O5^iii	90.16 (7)
C24—C25—H25	120.1	O6^iii—Mn1—O5^iii	57.52 (6)
C26—C25—H25	120.1	O7—Mn1—O5^iii	91.92 (8)
C25—C26—C21	121.1 (2)	O3—Mn1—C39^iii	128.77 (8)
C25—C26—H26	119.5	O4^ii—Mn1—C39^iii	88.64 (7)
C21—C26—H26	119.5	O9—Mn1—C39^iii	118.76 (8)
C32—C27—C28	117.4 (3)	O6^iii—Mn1—C39^iii	28.87 (7)
C32—C27—C2	121.1 (2)	O7—Mn1—C39^iii	90.89 (8)
C28—C27—C2	121.5 (2)	O5^iii—Mn1—C39^iii	28.65 (6)
C29—C28—C27	121.1 (3)	C8—N1—C7	112.8 (2)
C29—C28—H28	119.5	C8—N1—C33	124.2 (2)
C27—C28—H28	119.5	C7—N1—C33	122.7 (2)
C30—C29—C28	120.6 (3)	C43—N2—C41	121.2 (4)
C30—C29—H29	119.7	C43—N2—C42	120.8 (4)
C28—C29—H29	119.7	C41—N2—C42	118.0 (4)
C31—C30—C29	119.3 (3)	C46—N3—C44	119.7 (3)
C31—C30—H30	120.3	C46—N3—C45	122.0 (3)
C29—C30—H30	120.3	C44—N3—C45	118.2 (3)
C30—C31—C32	120.6 (3)	C40—O3—Mn1	124.13 (16)
C30—C31—H31	119.7	C40—O4—Mn1^ii	130.13 (17)
C32—C31—H31	119.7	C39—O5—Mn1^i	85.80 (13)
C31—C32—C27	121.0 (3)	C39—O6—Mn1^i	94.08 (14)
C31—C32—H32	119.5	C43—O7—Mn1	124.8 (2)
C27—C32—H32	119.5	C47—O9—Mn1	131.5 (2)
C38—C33—C34	120.9 (2)	C47—O9—H9	107.8
C38—C33—N1	118.92 (19)	Mn1—O9—H9	117.2
C34—C33—N1	120.13 (19)
C6—C1—C2—C3	0.2 (3)	C2—C27—C28—C29	179.8 (2)
C8—C1—C2—C3	177.9 (2)	C27—C28—C29—C30	−0.3 (4)
C6—C1—C2—C27	−179.13 (19)	C28—C29—C30—C31	0.8 (5)
C8—C1—C2—C27	−1.5 (3)	C29—C30—C31—C32	−0.8 (5)
C1—C2—C3—C4	−1.2 (3)	C30—C31—C32—C27	0.2 (4)
C27—C2—C3—C4	178.18 (19)	C28—C27—C32—C31	0.3 (4)
C1—C2—C3—C21	178.91 (18)	C2—C27—C32—C31	−179.8 (2)
C27—C2—C3—C21	−1.8 (3)	C38—C33—C34—C35	0.8 (4)
C2—C3—C4—C5	−0.1 (3)	N1—C33—C34—C35	178.7 (2)
C21—C3—C4—C5	179.79 (19)	C33—C34—C35—C36	−0.6 (4)
C2—C3—C4—C15	−179.6 (2)	C33—C34—C35—C40	−178.9 (2)
C21—C3—C4—C15	0.3 (3)	C34—C35—C36—C37	−1.3 (4)
C3—C4—C5—C6	2.3 (3)	C40—C35—C36—C37	177.0 (2)
C15—C4—C5—C6	−178.21 (19)	C35—C36—C37—C38	3.0 (4)
C3—C4—C5—C9	−177.74 (19)	C35—C36—C37—C39	−175.5 (2)
C15—C4—C5—C9	1.7 (3)	C34—C33—C38—C37	0.9 (4)
C2—C1—C6—C5	2.2 (3)	N1—C33—C38—C37	−177.0 (2)
C8—C1—C6—C5	−175.9 (2)	C36—C37—C38—C33	−2.7 (4)
C2—C1—C6—C7	−176.29 (19)	C39—C37—C38—C33	175.8 (2)
C8—C1—C6—C7	5.6 (2)	C38—C37—C39—O5	−158.0 (2)
C4—C5—C6—C1	−3.4 (3)	C36—C37—C39—O5	20.5 (4)
C9—C5—C6—C1	176.7 (2)	C38—C37—C39—O6	21.1 (4)
C4—C5—C6—C7	174.8 (2)	C36—C37—C39—O6	−160.4 (2)
C9—C5—C6—C7	−5.1 (3)	C38—C37—C39—Mn1^i	24 (2)
C1—C6—C7—O2	176.7 (2)	C36—C37—C39—Mn1^i	−157.4 (18)
C5—C6—C7—O2	−1.6 (4)	C34—C35—C40—O4	−160.5 (2)
C1—C6—C7—N1	−2.8 (2)	C36—C35—C40—O4	21.2 (4)
C5—C6—C7—N1	178.9 (2)	C34—C35—C40—O3	21.6 (4)
C6—C1—C8—O1	172.0 (2)	C36—C35—C40—O3	−156.7 (2)
C2—C1—C8—O1	−5.9 (4)	O1—C8—N1—C7	−173.8 (2)
C6—C1—C8—N1	−6.4 (2)	C1—C8—N1—C7	4.8 (2)
C2—C1—C8—N1	175.7 (2)	O1—C8—N1—C33	−0.4 (4)
C6—C5—C9—C10	−61.9 (3)	C1—C8—N1—C33	178.11 (18)
C4—C5—C9—C10	118.2 (3)	O2—C7—N1—C8	179.0 (2)
C6—C5—C9—C14	114.5 (3)	C6—C7—N1—C8	−1.5 (2)
C4—C5—C9—C14	−65.4 (3)	O2—C7—N1—C33	5.5 (3)
C14—C9—C10—C11	−1.8 (4)	C6—C7—N1—C33	−174.95 (18)
C5—C9—C10—C11	174.7 (3)	C38—C33—N1—C8	−59.7 (3)
C9—C10—C11—C12	−0.5 (5)	C34—C33—N1—C8	122.4 (3)
C10—C11—C12—C13	1.9 (6)	C38—C33—N1—C7	113.0 (3)
C11—C12—C13—C14	−1.1 (5)	C34—C33—N1—C7	−64.9 (3)
C12—C13—C14—C9	−1.3 (5)	O7—C43—N2—C41	−0.2 (6)
C10—C9—C14—C13	2.7 (4)	O7—C43—N2—C42	−179.3 (3)
C5—C9—C14—C13	−173.8 (3)	O8—C46—N3—C44	−0.5 (5)
C3—C4—C15—C16	119.3 (3)	O8—C46—N3—C45	176.9 (3)
C5—C4—C15—C16	−60.1 (3)	O4—C40—O3—Mn1	−7.8 (4)
C3—C4—C15—C20	−59.9 (3)	C35—C40—O3—Mn1	169.92 (15)
C5—C4—C15—C20	120.6 (3)	O4^ii—Mn1—O3—C40	56.7 (2)
C20—C15—C16—C17	1.0 (4)	O9—Mn1—O3—C40	−37.3 (2)
C4—C15—C16—C17	−178.3 (3)	O6^iii—Mn1—O3—C40	149.1 (2)
C15—C16—C17—C18	0.0 (5)	O7—Mn1—O3—C40	−122.9 (2)
C16—C17—C18—C19	−0.9 (5)	O5^iii—Mn1—O3—C40	156.97 (19)
C17—C18—C19—C20	0.7 (5)	C39^iii—Mn1—O3—C40	150.93 (19)
C18—C19—C20—C15	0.3 (5)	O3—C40—O4—Mn1^ii	−91.2 (3)
C16—C15—C20—C19	−1.2 (4)	C35—C40—O4—Mn1^ii	91.1 (2)
C4—C15—C20—C19	178.1 (3)	O6—C39—O5—Mn1^i	1.2 (3)
C4—C3—C21—C26	111.6 (3)	C37—C39—O5—Mn1^i	−179.8 (2)
C2—C3—C21—C26	−68.4 (3)	O5—C39—O6—Mn1^i	−1.3 (3)
C4—C3—C21—C22	−66.6 (3)	C37—C39—O6—Mn1^i	179.67 (19)
C2—C3—C21—C22	113.3 (3)	N2—C43—O7—Mn1	−172.9 (2)
C26—C21—C22—C23	−1.0 (4)	O3—Mn1—O7—C43	−17.8 (3)
C3—C21—C22—C23	177.3 (3)	O4^ii—Mn1—O7—C43	180 (100)
C21—C22—C23—C24	−0.2 (5)	O9—Mn1—O7—C43	−130.2 (3)
C22—C23—C24—C25	1.1 (5)	O6^iii—Mn1—O7—C43	82.3 (3)
C23—C24—C25—C26	−0.8 (5)	O5^iii—Mn1—O7—C43	139.7 (3)
C24—C25—C26—C21	−0.4 (5)	C39^iii—Mn1—O7—C43	111.1 (3)
C22—C21—C26—C25	1.3 (4)	O3—Mn1—O9—C47	15.3 (4)
C3—C21—C26—C25	−177.0 (3)	O4^ii—Mn1—O9—C47	−83.1 (3)
C1—C2—C27—C32	−49.3 (3)	O6^iii—Mn1—O9—C47	−176.5 (3)
C3—C2—C27—C32	131.4 (2)	O7—Mn1—O9—C47	97.9 (3)
C1—C2—C27—C28	130.6 (2)	O5^iii—Mn1—O9—C47	−170.2 (3)
C3—C2—C27—C28	−48.7 (3)	C39^iii—Mn1—O9—C47	−172.0 (3)
C32—C27—C28—C29	−0.3 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O8^ii	0.93	1.71	2.617 (3)	163

Symmetry code: (ii) −x−1, −y, −z.