μ3-Methoxido-κ(3) O:O:O-tris-(μ-l-p-tyrosinato-κ(3) N,O:O)tris-(l-p-tyrosinato-κ(2) N,O)trinickel(II,III) methanol tetra-solvate.

A trinuclear nickel complex, [Ni3(C9H10NO3)6(CH3O)]·4CH4O, was synthesized and characterized as a neutral cluster containing the incomplete cubane {Ni3(μ1-O)(μ2-O)2(μ3-O)} core of 2M3-1 topology. The three nickel cations show similar octa-hedral coordination, {Ni(μ1-O)(μ2-O)2(μ3-O)(μ1-N)2}; the positive charge is balanced by six tyrosinate ligands and one methoxide ion. The mean oxidation state of each Ni(II) ion is therefore +2.33. The common coordination modes, chelating (via the amino N and the carboxyl-ate O atoms) and bridging (via the carboxyl-ate O atom), are exhibited by the tyrosinates. Three inter-ligand (intra-cluster) N-H⋯O hydrogen-bonding inter-actions stabilize the incomplete cubane-type moiety. Additional N-H⋯O, O-H⋯O and C-H⋯O inter-actions are formed between clusters, and between the clusters and methanol mol-ecules to regulate the spatial orientation of the tyrosinate and the assembly of the clusters in the crystal. The approximate equilateral triangular arrangement of the three nickel cations in the incomplete cubane-type moiety suggests the possible magnetic frustration, and the proximity of these metal cations indicates weak metallic bonds. The structure contains approximately 39% solvent-accessible volume between the clusters. This is filled with 17 mol-ecules of disordered methanol and was modelled with SQUEEZE [Spek (2009 ▶). Acta Cryst. D65, 148-155]; the reported unit-cell characteristics do not take these mol-ecules into account. The H atoms of the solvent mol-ecules have not been included in the crystal data.

Related literature

For related incomplete cubane clusters, see: Ama et al. (2000 ▶); Lalia-Kantouri et al. (2010 ▶). For a nickel complex with l-tyrosine, see: Pei & Wang (2006 ▶). For structures with tyrosinate, see: Wojciechowska et al. (2011 ▶, 2012 ▶). For assignment of topology, see: Blatov (2012 ▶). For background to magnetic frustration, see: Hendrickson et al. (2005 ▶); Nakatsuji et al. (2005 ▶). For the CSD, see: Allen (2002 ▶).

Experimental

Crystal data

[Ni3(C9H10NO3)6(CH3O)]·4CH4O

M = 1400.28

Monoclinic,

a = 12.5688 (6) Å

b = 25.3381 (9) Å

c = 13.1058 (7) Å

β = 96.740 (4)°

V = 4145.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 150 K

0.36 × 0.35 × 0.34 mm

Data collection

Stoe IPDS2 diffractometer

Absorption correction: analytical (a face-indexed absorption correction was applied using the Tompa method; Meulenaer de & Tompa, 1965 ▶) T min = 0.716, T max = 0.780

41350 measured reflections

16565 independent reflections

11845 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 0.88

16565 reflections

780 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 8080 Friedel pairs

Flack parameter: 0.023 (9)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010696/tk5221sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010696/tk5221Isup2.hkl

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

[Ni3(C9H10NO3)6(CH3O)]·4CH4O	F(000) = 1454
Mr = 1400.28	Dx = 1.122 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3495 reflections
a = 12.5688 (6) Å	θ = 1.6–28.3°
b = 25.3381 (9) Å	µ = 0.74 mm−1
c = 13.1058 (7) Å	T = 150 K
β = 96.740 (4)°	Block, light-blue
V = 4145.0 (3) Å3	0.36 × 0.35 × 0.34 mm
Z = 2

Stoe IPDS2 diffractometer	16565 independent reflections
Radiation source: fine-focus sealed tube	11845 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 6.67 pixels mm-1	θmax = 26.1°, θmin = 1.6°
ω scans	h = −15→15
Absorption correction: analytical (a face-indexed absorption correction was applied using the Tompa method; Meulenaer de & Tompa, 1965)	k = −31→31
Tmin = 0.716, Tmax = 0.780	l = −16→14
41350 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88	(Δ/σ)max = 0.002
16565 reflections	Δρmax = 0.83 e Å−3
780 parameters	Δρmin = −0.38 e Å−3
1 restraint	Absolute structure: Flack (1983), 8080 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.023 (9)

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
Ni1	0.67401 (3)	0.209152 (16)	0.66058 (4)	0.03463 (11)
O1M	0.64605 (17)	0.28831 (10)	0.62163 (19)	0.0350 (5)
N1	0.7077 (2)	0.21031 (14)	0.8182 (2)	0.0432 (7)
H1A	0.6691	0.2359	0.8440	0.052*
H1B	0.6884	0.1793	0.8439	0.052*
O1	0.83540 (19)	0.22349 (9)	0.6684 (2)	0.0369 (6)
C1	0.8803 (3)	0.23246 (14)	0.7588 (3)	0.0404 (9)
O2	0.9740 (2)	0.25142 (11)	0.7761 (2)	0.0483 (7)
C2	0.8238 (3)	0.21973 (14)	0.8507 (3)	0.0426 (9)
H2	0.8296	0.2507	0.8958	0.051*
C3	0.8785 (3)	0.17307 (16)	0.9118 (3)	0.0477 (10)
H3A	0.9498	0.1841	0.9403	0.057*
H3B	0.8385	0.1655	0.9691	0.057*
C4	0.8886 (3)	0.12271 (16)	0.8527 (3)	0.0478 (10)
C5	0.9647 (3)	0.11715 (17)	0.7819 (4)	0.0558 (11)
H5	1.0082	0.1459	0.7713	0.067*
C6	0.9773 (4)	0.07274 (18)	0.7297 (4)	0.0614 (12)
H6	1.0295	0.0707	0.6851	0.074*
C7	0.9103 (4)	0.02862 (17)	0.7426 (4)	0.0590 (12)
C8	0.8360 (4)	0.03291 (17)	0.8129 (4)	0.0612 (13)
H8	0.7916	0.0046	0.8234	0.073*
C9	0.8280 (3)	0.07957 (17)	0.8676 (4)	0.0567 (11)
H9	0.7795	0.0813	0.9159	0.068*
O3	0.9161 (3)	−0.01815 (12)	0.6914 (3)	0.0763 (10)
H3	0.9644	−0.0166	0.6545	0.114*
N2	0.6949 (2)	0.12825 (11)	0.6396 (3)	0.0416 (8)
H2A	0.7321	0.1140	0.6957	0.050*
H2B	0.6310	0.1120	0.6282	0.050*
O4	0.66026 (18)	0.20168 (9)	0.5025 (2)	0.0370 (6)
C10	0.7201 (3)	0.16670 (13)	0.4722 (3)	0.0363 (9)
O5	0.7561 (2)	0.16689 (11)	0.3872 (2)	0.0455 (6)
C11	0.7544 (3)	0.12247 (13)	0.5498 (3)	0.0405 (9)
H11	0.8301	0.1285	0.5743	0.049*
C12	0.7462 (3)	0.06642 (14)	0.5046 (4)	0.0524 (11)
H12A	0.7801	0.0660	0.4418	0.063*
H12B	0.7859	0.0425	0.5527	0.063*
C13	0.6346 (3)	0.04650 (13)	0.4814 (3)	0.0420 (9)
C14	0.5666 (3)	0.06193 (14)	0.3962 (4)	0.0467 (10)
H14	0.5922	0.0858	0.3509	0.056*
C15	0.4626 (3)	0.04394 (14)	0.3745 (4)	0.0473 (10)
H15	0.4191	0.0556	0.3166	0.057*
C16	0.4246 (3)	0.00790 (15)	0.4418 (3)	0.0476 (10)
C17	0.4897 (3)	−0.00772 (15)	0.5270 (3)	0.0469 (10)
H17	0.4648	−0.0318	0.5723	0.056*
C18	0.5934 (3)	0.01222 (16)	0.5464 (3)	0.0501 (10)
H18	0.6360	0.0018	0.6059	0.060*
O6	0.3242 (2)	−0.01120 (10)	0.4159 (2)	0.0552 (8)
H6A	0.3093	−0.0318	0.4604	0.083*
Ni2	0.48220 (3)	0.291099 (15)	0.62530 (4)	0.03586 (11)
N3	0.4712 (2)	0.37166 (11)	0.6007 (2)	0.0358 (7)
H3C	0.5228	0.3820	0.5629	0.043*
H3D	0.4074	0.3794	0.5653	0.043*
O7	0.4971 (2)	0.31369 (9)	0.7749 (2)	0.0407 (6)
C19	0.5061 (3)	0.36282 (14)	0.7897 (3)	0.0404 (9)
O8	0.5333 (3)	0.38163 (11)	0.8774 (2)	0.0601 (8)
C20	0.4830 (3)	0.40097 (13)	0.7005 (3)	0.0368 (8)
H20	0.5445	0.4248	0.7010	0.044*
C21	0.3828 (3)	0.43479 (14)	0.7125 (3)	0.0423 (9)
H21A	0.3888	0.4487	0.7819	0.051*
H21B	0.3813	0.4645	0.6658	0.051*
C22	0.2789 (3)	0.40506 (13)	0.6917 (3)	0.0390 (9)
C23	0.2428 (3)	0.37308 (15)	0.7650 (3)	0.0451 (9)
H23	0.2813	0.3720	0.8301	0.054*
C24	0.1507 (3)	0.34206 (15)	0.7456 (3)	0.0434 (9)
H24	0.1278	0.3210	0.7969	0.052*
C25	0.0942 (3)	0.34335 (15)	0.6479 (3)	0.0428 (9)
C26	0.1283 (3)	0.37557 (17)	0.5735 (4)	0.0528 (11)
H26	0.0900	0.3769	0.5084	0.063*
C27	0.2194 (3)	0.40591 (15)	0.5956 (4)	0.0479 (10)
H27	0.2415	0.4275	0.5447	0.058*
O9	0.0065 (2)	0.31212 (11)	0.6231 (2)	0.0548 (7)
H9A	−0.0056	0.2951	0.6737	0.082*
N4	0.3258 (2)	0.26513 (11)	0.6264 (3)	0.0389 (7)
H4A	0.2840	0.2915	0.6447	0.047*
H4B	0.2991	0.2535	0.5637	0.047*
O10	0.50697 (18)	0.21246 (10)	0.6586 (2)	0.0396 (6)
C28	0.4328 (3)	0.18951 (14)	0.6989 (3)	0.0360 (8)
O11	0.4391 (2)	0.14462 (10)	0.7387 (2)	0.0448 (6)
C29	0.3300 (3)	0.22191 (14)	0.7017 (3)	0.0394 (9)
H29	0.3360	0.2387	0.7695	0.047*
C30	0.2260 (3)	0.18813 (15)	0.6932 (3)	0.0425 (9)
H30A	0.2380	0.1583	0.7394	0.051*
H30B	0.1693	0.2093	0.7166	0.051*
C31	0.1882 (3)	0.16788 (15)	0.5888 (3)	0.0462 (10)
C32	0.0857 (3)	0.18068 (18)	0.5424 (4)	0.0610 (13)
H32	0.0437	0.2038	0.5756	0.073*
C33	0.0455 (4)	0.16009 (19)	0.4494 (4)	0.0635 (13)
H33	−0.0248	0.1676	0.4228	0.076*
C34	0.1067 (4)	0.1288 (2)	0.3951 (4)	0.0661 (13)
C35	0.2115 (4)	0.1169 (2)	0.4365 (5)	0.0740 (16)
H35	0.2556	0.0973	0.3986	0.089*
C36	0.2488 (3)	0.13418 (18)	0.5326 (4)	0.0577 (12)
H36	0.3163	0.1234	0.5618	0.069*
O12	0.0715 (3)	0.10594 (17)	0.3024 (3)	0.0922 (12)
H12	0.0108	0.1164	0.2828	0.138*
Ni3	0.64300 (3)	0.280740 (15)	0.46105 (4)	0.03642 (11)
N5	0.8050 (2)	0.28923 (12)	0.4539 (2)	0.0386 (7)
H5A	0.8411	0.2779	0.5133	0.046*
H5B	0.8243	0.2689	0.4029	0.046*
O13	0.64711 (19)	0.36165 (10)	0.4467 (2)	0.0436 (7)
C37	0.7391 (3)	0.38049 (14)	0.4409 (3)	0.0422 (9)
O14	0.7563 (2)	0.42996 (10)	0.4409 (3)	0.0553 (8)
C38	0.8346 (3)	0.34438 (14)	0.4360 (3)	0.0437 (10)
H38	0.8876	0.3543	0.4937	0.052*
C39	0.8885 (3)	0.35072 (18)	0.3408 (4)	0.0565 (11)
H39A	0.9092	0.3874	0.3347	0.068*
H39B	0.9534	0.3297	0.3476	0.068*
C40	0.8211 (3)	0.33499 (17)	0.2459 (4)	0.0558 (11)
C41	0.7431 (4)	0.3691 (2)	0.1951 (4)	0.0692 (14)
H41	0.7337	0.4022	0.2234	0.083*
C42	0.6809 (4)	0.3557 (2)	0.1066 (4)	0.0690 (13)
H42	0.6305	0.3795	0.0763	0.083*
C43	0.6922 (3)	0.30699 (17)	0.0614 (3)	0.0530 (11)
C44	0.7645 (4)	0.27061 (18)	0.1084 (3)	0.0602 (12)
H44	0.7697	0.2370	0.0807	0.072*
C45	0.8300 (3)	0.2852 (2)	0.1989 (3)	0.0555 (10)
H45	0.8807	0.2613	0.2285	0.067*
O15	0.6373 (3)	0.29244 (14)	−0.0297 (2)	0.0757 (9)
H15A	0.5968	0.3163	−0.0512	0.114*
N6	0.5834 (3)	0.26790 (13)	0.3064 (3)	0.0452 (8)
H6B	0.5877	0.2980	0.2706	0.054*
H6C	0.6232	0.2432	0.2793	0.054*
O16	0.48472 (19)	0.27843 (10)	0.4722 (2)	0.0409 (6)
C46	0.4195 (3)	0.26377 (15)	0.3922 (3)	0.0444 (9)
O17	0.3229 (2)	0.26011 (14)	0.3935 (3)	0.0698 (9)
C47	0.4695 (3)	0.25007 (15)	0.2987 (3)	0.0442 (9)
H47	0.4292	0.2676	0.2395	0.053*
C48	0.4619 (3)	0.18945 (15)	0.2818 (3)	0.0463 (10)
H48A	0.5085	0.1722	0.3361	0.056*
H48B	0.3891	0.1783	0.2880	0.056*
C49	0.4916 (3)	0.17103 (14)	0.1804 (3)	0.0416 (9)
C50	0.4162 (3)	0.17076 (15)	0.0914 (3)	0.0483 (10)
H50	0.3466	0.1820	0.0961	0.058*
C51	0.4432 (3)	0.15440 (15)	−0.0011 (3)	0.0452 (9)
H51	0.3914	0.1545	−0.0580	0.054*
C52	0.5463 (3)	0.13756 (15)	−0.0125 (3)	0.0435 (9)
C53	0.6209 (3)	0.13709 (17)	0.0737 (3)	0.0522 (11)
H53	0.6900	0.1252	0.0684	0.063*
C54	0.5945 (3)	0.15397 (16)	0.1677 (3)	0.0481 (10)
H54	0.6469	0.1539	0.2240	0.058*
O18	0.5789 (2)	0.12088 (11)	−0.1018 (2)	0.0493 (7)
H18A	0.5288	0.1227	−0.1478	0.074*
O3M	1.0553 (3)	−0.02010 (15)	0.5593 (3)	0.0815 (10)*
C1M	0.7126 (3)	0.32667 (13)	0.6751 (3)	0.0384 (9)
H1M1	0.7859	0.3200	0.6652	0.058*
H1M2	0.7049	0.3250	0.7470	0.058*
H1M3	0.6923	0.3611	0.6492	0.058*
O2M	0.8596 (5)	0.1098 (2)	0.2522 (4)	0.1298 (17)*
C3M	1.0306 (5)	0.0038 (3)	0.4648 (5)	0.0954 (18)*
C2M	0.8170 (8)	0.0539 (4)	0.2325 (7)	0.140 (3)*
O4M	0.6264 (6)	0.4805 (3)	0.9009 (6)	0.177 (3)*
C4M	0.5490 (9)	0.5181 (5)	0.9249 (9)	0.172 (4)*
O5M	0.3634 (7)	0.3045 (4)	1.0147 (6)	0.215 (3)*
C5M	0.2700 (8)	0.3219 (4)	1.0342 (7)	0.142 (3)*

	U11	U22	U33	U12	U13	U23
Ni1	0.0304 (2)	0.0249 (2)	0.0472 (3)	−0.00070 (19)	−0.0011 (2)	−0.0033 (2)
O1M	0.0297 (11)	0.0255 (12)	0.0488 (14)	−0.0037 (11)	−0.0001 (11)	−0.0059 (13)
N1	0.0360 (15)	0.0412 (16)	0.053 (2)	−0.0085 (15)	0.0067 (14)	−0.0080 (17)
O1	0.0336 (12)	0.0317 (13)	0.0440 (16)	−0.0004 (10)	−0.0013 (12)	−0.0034 (11)
C1	0.0353 (19)	0.0343 (18)	0.050 (3)	−0.0008 (16)	−0.0009 (19)	−0.0015 (18)
O2	0.0377 (14)	0.0554 (16)	0.0489 (18)	−0.0156 (12)	−0.0075 (12)	0.0015 (13)
C2	0.0403 (18)	0.039 (2)	0.048 (2)	−0.0038 (16)	0.0012 (17)	−0.0046 (17)
C3	0.043 (2)	0.053 (2)	0.047 (3)	−0.0058 (18)	0.0026 (19)	0.005 (2)
C4	0.044 (2)	0.045 (2)	0.052 (3)	0.0069 (18)	−0.0030 (19)	0.0143 (19)
C5	0.048 (2)	0.051 (2)	0.066 (3)	0.001 (2)	−0.001 (2)	0.016 (2)
C6	0.061 (3)	0.060 (3)	0.065 (3)	0.022 (2)	0.014 (2)	0.008 (2)
C7	0.062 (3)	0.043 (2)	0.072 (3)	0.015 (2)	0.007 (2)	0.014 (2)
C8	0.068 (3)	0.039 (2)	0.079 (4)	0.011 (2)	0.018 (3)	0.014 (2)
C9	0.043 (2)	0.054 (2)	0.075 (3)	0.0042 (19)	0.016 (2)	0.011 (2)
O3	0.092 (2)	0.0403 (16)	0.098 (3)	0.0149 (17)	0.017 (2)	−0.0075 (17)
N2	0.0390 (16)	0.0276 (15)	0.055 (2)	−0.0005 (13)	−0.0062 (16)	0.0028 (15)
O4	0.0306 (12)	0.0285 (13)	0.0505 (16)	−0.0010 (10)	−0.0018 (11)	−0.0048 (12)
C10	0.0255 (16)	0.0301 (17)	0.049 (3)	−0.0015 (14)	−0.0118 (17)	−0.0123 (17)
O5	0.0422 (14)	0.0469 (15)	0.0460 (18)	0.0047 (12)	−0.0009 (13)	−0.0061 (13)
C11	0.0377 (19)	0.0246 (16)	0.057 (3)	0.0008 (15)	−0.0040 (18)	−0.0050 (17)
C12	0.047 (2)	0.0325 (19)	0.074 (3)	0.0084 (17)	−0.009 (2)	−0.012 (2)
C13	0.044 (2)	0.0233 (17)	0.056 (3)	0.0032 (15)	−0.004 (2)	−0.0103 (17)
C14	0.045 (2)	0.0256 (17)	0.069 (3)	0.0033 (16)	0.003 (2)	−0.0084 (18)
C15	0.039 (2)	0.0322 (19)	0.067 (3)	0.0031 (16)	−0.009 (2)	−0.0080 (19)
C16	0.046 (2)	0.0349 (19)	0.061 (3)	0.0006 (17)	0.001 (2)	−0.0070 (19)
C17	0.056 (2)	0.0332 (19)	0.051 (3)	−0.0023 (18)	0.001 (2)	−0.0068 (18)
C18	0.049 (2)	0.042 (2)	0.055 (3)	0.0013 (18)	−0.013 (2)	−0.004 (2)
O6	0.0456 (15)	0.0383 (14)	0.079 (2)	−0.0074 (12)	−0.0034 (15)	−0.0070 (14)
Ni2	0.0298 (2)	0.0241 (2)	0.0525 (3)	−0.00098 (18)	0.0001 (2)	−0.0018 (2)
N3	0.0310 (15)	0.0288 (15)	0.046 (2)	0.0016 (12)	−0.0017 (14)	0.0017 (14)
O7	0.0397 (13)	0.0277 (12)	0.0528 (17)	−0.0013 (10)	−0.0032 (12)	0.0049 (11)
C19	0.0345 (18)	0.035 (2)	0.049 (3)	−0.0052 (15)	−0.0072 (18)	0.0006 (18)
O8	0.087 (2)	0.0409 (14)	0.0453 (18)	−0.0113 (15)	−0.0201 (16)	−0.0072 (14)
C20	0.0369 (19)	0.0251 (16)	0.047 (2)	−0.0045 (15)	−0.0018 (17)	−0.0022 (16)
C21	0.040 (2)	0.0293 (17)	0.055 (3)	−0.0007 (15)	−0.0047 (18)	−0.0007 (17)
C22	0.0329 (18)	0.0289 (17)	0.055 (3)	0.0049 (15)	0.0039 (18)	0.0020 (17)
C23	0.038 (2)	0.049 (2)	0.047 (3)	−0.0048 (17)	0.0014 (19)	0.0023 (19)
C24	0.0348 (18)	0.048 (2)	0.046 (2)	−0.0067 (17)	0.0018 (18)	0.0051 (18)
C25	0.0280 (17)	0.046 (2)	0.054 (3)	0.0023 (16)	0.0039 (18)	0.0057 (19)
C26	0.036 (2)	0.054 (2)	0.065 (3)	0.0026 (18)	−0.009 (2)	0.025 (2)
C27	0.038 (2)	0.041 (2)	0.063 (3)	0.0026 (17)	0.001 (2)	0.017 (2)
O9	0.0318 (13)	0.0611 (17)	0.069 (2)	−0.0089 (12)	−0.0054 (13)	0.0149 (15)
N4	0.0329 (15)	0.0278 (14)	0.056 (2)	−0.0001 (12)	0.0029 (14)	−0.0076 (14)
O10	0.0294 (11)	0.0236 (11)	0.0647 (18)	−0.0029 (11)	0.0007 (12)	0.0042 (13)
C28	0.0399 (19)	0.0334 (18)	0.032 (2)	−0.0048 (15)	−0.0058 (16)	−0.0072 (16)
O11	0.0424 (14)	0.0324 (13)	0.0554 (18)	−0.0034 (11)	−0.0123 (13)	0.0062 (12)
C29	0.0352 (18)	0.041 (2)	0.041 (2)	−0.0084 (15)	−0.0010 (16)	−0.0060 (16)
C30	0.0379 (19)	0.0405 (19)	0.048 (3)	−0.0036 (16)	−0.0008 (18)	0.0030 (18)
C31	0.038 (2)	0.0355 (19)	0.063 (3)	−0.0091 (17)	−0.001 (2)	−0.0093 (19)
C32	0.049 (2)	0.059 (3)	0.071 (3)	0.015 (2)	−0.010 (2)	−0.023 (2)
C33	0.051 (2)	0.057 (3)	0.082 (4)	0.006 (2)	0.001 (3)	−0.014 (3)
C34	0.060 (3)	0.068 (3)	0.067 (3)	0.003 (2)	−0.009 (2)	−0.021 (3)
C35	0.050 (3)	0.064 (3)	0.106 (4)	0.004 (2)	0.001 (3)	−0.040 (3)
C36	0.033 (2)	0.059 (3)	0.077 (3)	0.0037 (19)	−0.011 (2)	−0.029 (2)
O12	0.081 (3)	0.101 (3)	0.090 (3)	0.010 (2)	−0.006 (2)	−0.033 (2)
Ni3	0.0310 (2)	0.0278 (2)	0.0490 (3)	−0.00175 (18)	−0.0016 (2)	−0.0004 (2)
N5	0.0376 (15)	0.0345 (15)	0.0420 (17)	0.0044 (15)	−0.0027 (13)	−0.0044 (15)
O13	0.0316 (13)	0.0301 (13)	0.067 (2)	−0.0019 (11)	−0.0009 (13)	0.0051 (13)
C37	0.044 (2)	0.0297 (18)	0.052 (3)	−0.0033 (16)	0.0003 (19)	0.0033 (17)
O14	0.0427 (15)	0.0307 (13)	0.091 (2)	−0.0059 (12)	0.0022 (15)	0.0084 (14)
C38	0.0322 (18)	0.0358 (19)	0.064 (3)	−0.0066 (15)	0.0073 (19)	−0.0021 (18)
C39	0.051 (2)	0.051 (2)	0.068 (3)	−0.008 (2)	0.008 (2)	−0.003 (2)
C40	0.040 (2)	0.053 (3)	0.074 (3)	−0.0022 (19)	0.009 (2)	0.008 (2)
C41	0.077 (3)	0.060 (3)	0.068 (4)	0.013 (3)	−0.004 (3)	0.011 (3)
C42	0.078 (3)	0.060 (3)	0.064 (3)	0.022 (3)	−0.011 (3)	0.004 (3)
C43	0.052 (2)	0.063 (3)	0.040 (2)	0.010 (2)	−0.007 (2)	0.008 (2)
C44	0.073 (3)	0.055 (3)	0.052 (3)	0.023 (2)	0.003 (2)	−0.001 (2)
C45	0.054 (2)	0.062 (3)	0.049 (2)	0.008 (2)	0.0030 (19)	0.004 (2)
O15	0.084 (2)	0.072 (2)	0.065 (2)	0.028 (2)	−0.0147 (17)	−0.0137 (19)
N6	0.0452 (17)	0.0402 (17)	0.048 (2)	−0.0112 (14)	−0.0028 (15)	0.0045 (15)
O16	0.0355 (12)	0.0340 (14)	0.0521 (16)	−0.0046 (12)	0.0008 (12)	−0.0027 (13)
C46	0.0300 (19)	0.045 (2)	0.054 (3)	−0.0014 (16)	−0.0109 (18)	0.0026 (19)
O17	0.0342 (16)	0.100 (3)	0.071 (2)	−0.0017 (15)	−0.0130 (14)	0.0005 (19)
C47	0.042 (2)	0.044 (2)	0.043 (3)	−0.0003 (17)	−0.0103 (18)	0.0034 (18)
C48	0.043 (2)	0.043 (2)	0.050 (3)	−0.0106 (17)	−0.0079 (19)	0.0107 (19)
C49	0.042 (2)	0.0322 (18)	0.048 (2)	−0.0059 (16)	−0.0057 (18)	0.0027 (17)
C50	0.0361 (19)	0.045 (2)	0.061 (3)	−0.0011 (17)	−0.0061 (19)	0.000 (2)
C51	0.040 (2)	0.051 (2)	0.040 (2)	−0.0015 (17)	−0.0104 (18)	0.0021 (19)
C52	0.043 (2)	0.043 (2)	0.044 (2)	−0.0086 (17)	0.0039 (19)	0.0094 (18)
C53	0.041 (2)	0.056 (2)	0.056 (3)	−0.0042 (19)	−0.009 (2)	0.019 (2)
C54	0.039 (2)	0.059 (3)	0.044 (3)	−0.0040 (19)	−0.0073 (19)	0.007 (2)
O18	0.0405 (14)	0.0566 (16)	0.0477 (18)	−0.0053 (13)	−0.0080 (13)	0.0044 (14)
C1M	0.0333 (17)	0.0302 (18)	0.051 (2)	−0.0019 (15)	0.0035 (17)	−0.0046 (17)

Ni1—O1	2.051 (2)	C27—H27	0.9300
Ni1—N1	2.060 (3)	O9—H9A	0.8200
Ni1—O4	2.067 (3)	N4—C29	1.471 (5)
Ni1—N2	2.089 (3)	N4—H4A	0.9000
Ni1—O1M	2.089 (3)	N4—H4B	0.9000
Ni1—O10	2.098 (2)	O10—C28	1.265 (4)
O1M—C1M	1.413 (4)	C28—O11	1.250 (4)
O1M—Ni2	2.067 (2)	C28—C29	1.535 (5)
O1M—Ni3	2.109 (2)	C29—C30	1.556 (5)
N1—C2	1.490 (5)	C29—H29	0.9800
N1—H1A	0.9000	C30—C31	1.486 (6)
N1—H1B	0.9000	C30—H30A	0.9700
O1—C1	1.272 (5)	C30—H30B	0.9700
C1—O2	1.268 (4)	C31—C32	1.397 (6)
C1—C2	1.504 (5)	C31—C36	1.409 (6)
C2—C3	1.544 (5)	C32—C33	1.367 (6)
C2—H2	0.9800	C32—H32	0.9300
C3—C4	1.506 (6)	C33—C34	1.362 (6)
C3—H3A	0.9700	C33—H33	0.9300
C3—H3B	0.9700	C34—O12	1.371 (6)
C4—C9	1.360 (6)	C34—C35	1.397 (7)
C4—C5	1.415 (6)	C35—C36	1.363 (7)
C5—C6	1.336 (6)	C35—H35	0.9300
C5—H5	0.9300	C36—H36	0.9300
C6—C7	1.421 (6)	O12—H12	0.8200
C6—H6	0.9300	Ni3—O16	2.013 (2)
C7—O3	1.368 (5)	Ni3—O13	2.060 (3)
C7—C8	1.392 (6)	Ni3—N5	2.060 (3)
C8—C9	1.392 (6)	Ni3—N6	2.102 (3)
C8—H8	0.9300	N5—C38	1.472 (5)
C9—H9	0.9300	N5—H5A	0.9000
O3—H3	0.8200	N5—H5B	0.9000
N2—C11	1.473 (5)	O13—C37	1.261 (4)
N2—H2A	0.9000	C37—O14	1.272 (4)
N2—H2B	0.9000	C37—C38	1.517 (5)
O4—C10	1.256 (4)	C38—C39	1.497 (6)
O4—Ni3	2.080 (2)	C38—H38	0.9800
C10—O5	1.251 (4)	C39—C40	1.475 (7)
C10—C11	1.541 (5)	C39—H39A	0.9700
C11—C12	1.538 (5)	C39—H39B	0.9700
C11—H11	0.9800	C40—C41	1.413 (7)
C12—C13	1.488 (5)	C40—C45	1.414 (7)
C12—H12A	0.9700	C41—C42	1.363 (7)
C12—H12B	0.9700	C41—H41	0.9300
C13—C18	1.361 (6)	C42—C43	1.383 (7)
C13—C14	1.381 (6)	C42—H42	0.9300
C14—C15	1.382 (5)	C43—O15	1.358 (5)
C14—H14	0.9300	C43—C44	1.387 (6)
C15—C16	1.392 (6)	C44—C45	1.411 (6)
C15—H15	0.9300	C44—H44	0.9300
C16—O6	1.356 (5)	C45—H45	0.9300
C16—C17	1.364 (6)	O15—H15A	0.8200
C17—C18	1.393 (6)	N6—C47	1.494 (5)
C17—H17	0.9300	N6—H6B	0.9000
C18—H18	0.9300	N6—H6C	0.9000
O6—H6A	0.8200	O16—C46	1.307 (5)
Ni2—O7	2.030 (3)	C46—O17	1.219 (4)
Ni2—O16	2.036 (3)	C46—C47	1.483 (6)
Ni2—O10	2.056 (3)	C47—C48	1.553 (5)
Ni2—N3	2.069 (3)	C47—H47	0.9800
Ni2—N4	2.074 (3)	C48—C49	1.497 (6)
N3—C20	1.496 (5)	C48—H48A	0.9700
N3—H3C	0.9000	C48—H48B	0.9700
N3—H3D	0.9000	C49—C54	1.392 (5)
O7—C19	1.263 (4)	C49—C50	1.414 (5)
C19—O8	1.255 (5)	C50—C51	1.361 (6)
C19—C20	1.518 (5)	C50—H50	0.9300
C20—C21	1.546 (5)	C51—C52	1.390 (5)
C20—H20	0.9800	C51—H51	0.9300
C21—C22	1.505 (5)	C52—O18	1.352 (5)
C21—H21A	0.9700	C52—C53	1.381 (6)
C21—H21B	0.9700	C53—C54	1.381 (6)
C22—C23	1.374 (5)	C53—H53	0.9300
C22—C27	1.387 (6)	C54—H54	0.9300
C23—C24	1.398 (5)	O18—H18A	0.8200
C23—H23	0.9300	O3M—C3M	1.382 (7)
C24—C25	1.390 (6)	C1M—H1M1	0.9600
C24—H24	0.9300	C1M—H1M2	0.9600
C25—O9	1.365 (5)	C1M—H1M3	0.9600
C25—C26	1.378 (6)	O2M—C2M	1.526 (10)
C26—C27	1.382 (6)	O4M—C4M	1.423 (12)
C26—H26	0.9300	O5M—C5M	1.306 (11)
O1—Ni1—N1	82.06 (11)	C25—C26—H26	120.0
O1—Ni1—O4	91.83 (10)	C27—C26—H26	120.0
N1—Ni1—O4	171.72 (11)	C26—C27—C22	121.8 (4)
O1—Ni1—N2	92.38 (11)	C26—C27—H27	119.1
N1—Ni1—N2	97.58 (14)	C22—C27—H27	119.1
O4—Ni1—N2	77.00 (12)	C25—O9—H9A	109.5
O1—Ni1—O1M	88.80 (9)	C29—N4—Ni2	106.4 (2)
N1—Ni1—O1M	103.90 (12)	C29—N4—H4A	110.5
O4—Ni1—O1M	81.44 (9)	Ni2—N4—H4A	110.5
N2—Ni1—O1M	158.43 (11)	C29—N4—H4B	110.5
O1—Ni1—O10	167.32 (10)	Ni2—N4—H4B	110.5
N1—Ni1—O10	95.69 (11)	H4A—N4—H4B	108.6
O4—Ni1—O10	91.47 (10)	C28—O10—Ni2	115.7 (2)
N2—Ni1—O10	100.29 (11)	C28—O10—Ni1	139.6 (2)
O1M—Ni1—O10	79.59 (9)	Ni2—O10—Ni1	99.64 (10)
C1M—O1M—Ni2	119.9 (2)	O11—C28—O10	125.3 (3)
C1M—O1M—Ni1	117.8 (2)	O11—C28—C29	119.3 (3)
Ni2—O1M—Ni1	99.59 (10)	O10—C28—C29	115.3 (3)
C1M—O1M—Ni3	119.8 (2)	N4—C29—C28	110.2 (3)
Ni2—O1M—Ni3	97.17 (10)	N4—C29—C30	113.5 (3)
Ni1—O1M—Ni3	98.01 (10)	C28—C29—C30	114.0 (3)
C2—N1—Ni1	111.6 (2)	N4—C29—H29	106.2
C2—N1—H1A	109.3	C28—C29—H29	106.2
Ni1—N1—H1A	109.3	C30—C29—H29	106.2
C2—N1—H1B	109.3	C31—C30—C29	115.5 (3)
Ni1—N1—H1B	109.3	C31—C30—H30A	108.4
H1A—N1—H1B	108.0	C29—C30—H30A	108.4
C1—O1—Ni1	114.0 (2)	C31—C30—H30B	108.4
O2—C1—O1	122.4 (4)	C29—C30—H30B	108.4
O2—C1—C2	117.0 (4)	H30A—C30—H30B	107.5
O1—C1—C2	120.6 (3)	C32—C31—C36	116.2 (4)
N1—C2—C1	110.1 (3)	C32—C31—C30	120.0 (4)
N1—C2—C3	112.8 (3)	C36—C31—C30	123.8 (4)
C1—C2—C3	110.8 (3)	C33—C32—C31	121.7 (4)
N1—C2—H2	107.6	C33—C32—H32	119.2
C1—C2—H2	107.6	C31—C32—H32	119.2
C3—C2—H2	107.6	C34—C33—C32	121.0 (4)
C4—C3—C2	116.2 (3)	C34—C33—H33	119.5
C4—C3—H3A	108.2	C32—C33—H33	119.5
C2—C3—H3A	108.2	C33—C34—O12	124.4 (4)
C4—C3—H3B	108.2	C33—C34—C35	119.1 (5)
C2—C3—H3B	108.2	O12—C34—C35	116.4 (4)
H3A—C3—H3B	107.4	C36—C35—C34	119.8 (4)
C9—C4—C5	116.6 (4)	C36—C35—H35	120.1
C9—C4—C3	121.6 (4)	C34—C35—H35	120.1
C5—C4—C3	121.7 (4)	C35—C36—C31	121.9 (4)
C6—C5—C4	123.3 (4)	C35—C36—H36	119.1
C6—C5—H5	118.4	C31—C36—H36	119.1
C4—C5—H5	118.4	C34—O12—H12	109.5
C5—C6—C7	119.6 (4)	O16—Ni3—O13	94.09 (10)
C5—C6—H6	120.2	O16—Ni3—N5	175.41 (12)
C7—C6—H6	120.2	O13—Ni3—N5	81.74 (11)
O3—C7—C8	118.1 (4)	O16—Ni3—O4	91.53 (10)
O3—C7—C6	123.8 (4)	O13—Ni3—O4	168.31 (11)
C8—C7—C6	118.1 (4)	N5—Ni3—O4	92.24 (11)
C7—C8—C9	120.1 (4)	O16—Ni3—N6	79.74 (12)
C7—C8—H8	119.9	O13—Ni3—N6	94.34 (12)
C9—C8—H8	119.9	N5—Ni3—N6	102.40 (12)
C4—C9—C8	122.2 (4)	O4—Ni3—N6	96.75 (11)
C4—C9—H9	118.9	O16—Ni3—O1M	80.37 (9)
C8—C9—H9	118.9	O13—Ni3—O1M	90.18 (11)
C7—O3—H3	109.5	N5—Ni3—O1M	97.66 (10)
C11—N2—Ni1	106.6 (2)	O4—Ni3—O1M	80.65 (10)
C11—N2—H2A	110.4	N6—Ni3—O1M	159.86 (10)
Ni1—N2—H2A	110.4	C38—N5—Ni3	112.1 (2)
C11—N2—H2B	110.4	C38—N5—H5A	109.2
Ni1—N2—H2B	110.4	Ni3—N5—H5A	109.2
H2A—N2—H2B	108.6	C38—N5—H5B	109.2
C10—O4—Ni1	113.5 (2)	Ni3—N5—H5B	109.2
C10—O4—Ni3	130.1 (2)	H5A—N5—H5B	107.9
Ni1—O4—Ni3	99.65 (10)	C37—O13—Ni3	114.5 (2)
O5—C10—O4	124.9 (4)	O13—C37—O14	122.0 (3)
O5—C10—C11	119.2 (3)	O13—C37—C38	120.7 (3)
O4—C10—C11	115.8 (3)	O14—C37—C38	117.3 (3)
N2—C11—C12	112.5 (3)	N5—C38—C39	112.5 (3)
N2—C11—C10	109.0 (3)	N5—C38—C37	110.4 (3)
C12—C11—C10	114.6 (3)	C39—C38—C37	114.1 (4)
N2—C11—H11	106.7	N5—C38—H38	106.4
C12—C11—H11	106.7	C39—C38—H38	106.4
C10—C11—H11	106.7	C37—C38—H38	106.4
C13—C12—C11	114.2 (3)	C40—C39—C38	113.7 (4)
C13—C12—H12A	108.7	C40—C39—H39A	108.8
C11—C12—H12A	108.7	C38—C39—H39A	108.8
C13—C12—H12B	108.7	C40—C39—H39B	108.8
C11—C12—H12B	108.7	C38—C39—H39B	108.8
H12A—C12—H12B	107.6	H39A—C39—H39B	107.7
C18—C13—C14	116.2 (4)	C41—C40—C45	115.2 (5)
C18—C13—C12	120.5 (4)	C41—C40—C39	122.0 (4)
C14—C13—C12	123.3 (4)	C45—C40—C39	122.8 (4)
C13—C14—C15	123.6 (4)	C42—C41—C40	123.1 (5)
C13—C14—H14	118.2	C42—C41—H41	118.5
C15—C14—H14	118.2	C40—C41—H41	118.5
C14—C15—C16	118.2 (4)	C41—C42—C43	120.6 (5)
C14—C15—H15	120.9	C41—C42—H42	119.7
C16—C15—H15	120.9	C43—C42—H42	119.7
O6—C16—C17	123.5 (4)	O15—C43—C42	123.4 (4)
O6—C16—C15	117.0 (4)	O15—C43—C44	116.7 (4)
C17—C16—C15	119.4 (4)	C42—C43—C44	119.9 (4)
C16—C17—C18	120.2 (4)	C43—C44—C45	119.1 (4)
C16—C17—H17	119.9	C43—C44—H44	120.5
C18—C17—H17	119.9	C45—C44—H44	120.5
C13—C18—C17	122.2 (4)	C44—C45—C40	122.1 (4)
C13—C18—H18	118.9	C44—C45—H45	118.9
C17—C18—H18	118.9	C40—C45—H45	118.9
C16—O6—H6A	109.5	C43—O15—H15A	109.5
O7—Ni2—O16	170.42 (10)	C47—N6—Ni3	110.1 (2)
O7—Ni2—O10	94.22 (10)	C47—N6—H6B	109.6
O16—Ni2—O10	92.13 (11)	Ni3—N6—H6B	109.6
O7—Ni2—O1M	93.04 (10)	C47—N6—H6C	109.6
O16—Ni2—O1M	80.85 (9)	Ni3—N6—H6C	109.6
O10—Ni2—O1M	81.11 (9)	H6B—N6—H6C	108.2
O7—Ni2—N3	82.47 (11)	C46—O16—Ni3	118.9 (2)
O16—Ni2—N3	90.61 (12)	C46—O16—Ni2	139.0 (2)
O10—Ni2—N3	174.38 (12)	Ni3—O16—Ni2	101.34 (11)
O1M—Ni2—N3	94.50 (11)	O17—C46—O16	122.8 (4)
O7—Ni2—N4	93.59 (11)	O17—C46—C47	120.9 (4)
O16—Ni2—N4	94.65 (11)	O16—C46—C47	116.3 (3)
O10—Ni2—N4	79.10 (10)	C46—C47—N6	111.6 (3)
O1M—Ni2—N4	159.52 (10)	C46—C47—C48	108.9 (3)
N3—Ni2—N4	105.56 (11)	N6—C47—C48	110.6 (3)
C20—N3—Ni2	110.8 (2)	C46—C47—H47	108.6
C20—N3—H3C	109.5	N6—C47—H47	108.6
Ni2—N3—H3C	109.5	C48—C47—H47	108.6
C20—N3—H3D	109.5	C49—C48—C47	114.6 (3)
Ni2—N3—H3D	109.5	C49—C48—H48A	108.6
H3C—N3—H3D	108.1	C47—C48—H48A	108.6
C19—O7—Ni2	115.0 (3)	C49—C48—H48B	108.6
O8—C19—O7	121.6 (4)	C47—C48—H48B	108.6
O8—C19—C20	118.1 (3)	H48A—C48—H48B	107.6
O7—C19—C20	120.3 (4)	C54—C49—C50	116.2 (4)
N3—C20—C19	110.3 (3)	C54—C49—C48	122.4 (4)
N3—C20—C21	111.5 (3)	C50—C49—C48	121.5 (4)
C19—C20—C21	111.0 (3)	C51—C50—C49	121.6 (4)
N3—C20—H20	108.0	C51—C50—H50	119.2
C19—C20—H20	108.0	C49—C50—H50	119.2
C21—C20—H20	108.0	C50—C51—C52	121.5 (4)
C22—C21—C20	113.8 (3)	C50—C51—H51	119.3
C22—C21—H21A	108.8	C52—C51—H51	119.3
C20—C21—H21A	108.8	O18—C52—C53	117.4 (4)
C22—C21—H21B	108.8	O18—C52—C51	124.8 (4)
C20—C21—H21B	108.8	C53—C52—C51	117.8 (4)
H21A—C21—H21B	107.7	C54—C53—C52	121.1 (4)
C23—C22—C27	117.2 (3)	C54—C53—H53	119.5
C23—C22—C21	121.2 (4)	C52—C53—H53	119.5
C27—C22—C21	121.4 (3)	C53—C54—C49	121.8 (4)
C22—C23—C24	122.6 (4)	C53—C54—H54	119.1
C22—C23—H23	118.7	C49—C54—H54	119.1
C24—C23—H23	118.7	C52—O18—H18A	109.5
C25—C24—C23	118.5 (4)	O1M—C1M—H1M1	109.5
C25—C24—H24	120.7	O1M—C1M—H1M2	109.5
C23—C24—H24	120.7	H1M1—C1M—H1M2	109.5
O9—C25—C26	119.0 (4)	O1M—C1M—H1M3	109.5
O9—C25—C24	121.2 (3)	H1M1—C1M—H1M3	109.5
C26—C25—C24	119.8 (4)	H1M2—C1M—H1M3	109.5
C25—C26—C27	120.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O15i	0.90	2.26	3.082 (4)	153
N1—H1B···O18i	0.90	2.20	3.042 (4)	157
O3—H3···O3M	0.82	1.79	2.601 (5)	170
O6—H6A···O14ii	0.82	1.88	2.685 (4)	166
N3—H3C···O13	0.90	2.36	3.174 (4)	150
O9—H9A···O2iii	0.82	1.78	2.597 (4)	173
N4—H4B···O17	0.90	2.29	3.050 (5)	142
O12—H12···O2Miii	0.82	1.90	2.669 (7)	155
N5—H5A···O1	0.90	2.46	3.251 (4)	146
N5—H5A···O9iv	0.90	2.54	3.216 (4)	133
O15—H15A···O8v	0.82	2.02	2.815 (4)	164
O15—H15A···O7v	0.82	2.47	2.983 (4)	122
O18—H18A···O11v	0.82	1.84	2.638 (4)	163
C1M—H1M1···O1	0.96	2.52	3.042 (4)	114
C30—H30A···O11	0.97	2.55	2.893 (5)	101
C38—H38···O9iv	0.98	2.38	3.178 (5)	138
C54—H54···O5	0.93	2.42	3.338 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O15i	0.90	2.26	3.082 (4)	153
N1—H1B⋯O18i	0.90	2.20	3.042 (4)	157
O3—H3⋯O3M	0.82	1.79	2.601 (5)	170
O6—H6A⋯O14ii	0.82	1.88	2.685 (4)	166
N3—H3C⋯O13	0.90	2.36	3.174 (4)	150
O9—H9A⋯O2iii	0.82	1.78	2.597 (4)	173
N4—H4B⋯O17	0.90	2.29	3.050 (5)	142
O12—H12⋯O2M iii	0.82	1.90	2.669 (7)	155
N5—H5A⋯O1	0.90	2.46	3.251 (4)	146
N5—H5A⋯O9iv	0.90	2.54	3.216 (4)	133
O15—H15A⋯O8v	0.82	2.02	2.815 (4)	164
O15—H15A⋯O7v	0.82	2.47	2.983 (4)	122
O18—H18A⋯O11v	0.82	1.84	2.638 (4)	163
C1M—H1M1⋯O1	0.96	2.52	3.042 (4)	114
C30—H30A⋯O11	0.97	2.55	2.893 (5)	101
C38—H38⋯O9iv	0.98	2.38	3.178 (5)	138
C54—H54⋯O5	0.93	2.42	3.338 (5)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .