Tetra-kis(μ-phenoxy-acetato-κO:O')bis-[(1,10-phenanthroline-κN,N')manganese(II)] methanol hemisolvate.

The title complex, [Mn(2)(C(8)H(7)O(3))(4)(C(12)H(8)N(2))(2)]·0.5CH(3)OH, is a carboxyl-ate-bridged dinuclear Mn(II) complex with four phenoxy-acetate ions and two 1,10-phenanthroline mol-ecules as ligands. Each of the four phenoxy-acetate anions bridges the pair of Mn atoms. The asymmetric unit is completed by a half-occupancy methanol solvent mol-ecule. Face-to-face π-π stacking inter-actions between the aromatic rings of 1,10-phenanthroline molecules belonging to adjacent Mn(2) complexes, with an inter-planar separation of circa 3.4 Å, and weak C-H⋯O hydrogen bonds connect the dinuclear units into a three-dimensional supra-molecular framework.

Related literature

For related literature, see: Jiang et al. (2005 ▶, 2006 ▶); Sessoli et al. (1993 ▶); Yaghi et al. (1997 ▶).

Experimental

Crystal data

[Mn2(C8H7O3)4(C12H8N2)2]·0.5CH4O

M = 1090.86

Triclinic,

a = 12.4627 (10) Å

b = 12.8334 (10) Å

c = 17.1377 (13) Å

α = 77.421 (1)°

β = 87.635 (1)°

γ = 84.629 (1)°

V = 2662.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 193 (2) K

0.30 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.848, T max = 0.879

14596 measured reflections

10273 independent reflections

6679 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.149

S = 1.08

10273 reflections

675 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065269/bh2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065269/bh2151Isup2.hkl

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

[Mn2(C8H7O3)4(C12H8N2)2]·0.5CH4O	Z = 2
Mr = 1090.86	F000 = 1126.0
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 12.4627 (10) Å	Cell parameters from 14596 reflections
b = 12.8334 (10) Å	θ = 2.4–28.1º
c = 17.1377 (13) Å	µ = 0.54 mm−1
α = 77.421 (1)º	T = 193 (2) K
β = 87.635 (1)º	Prism, light brown
γ = 84.629 (1)º	0.30 × 0.24 × 0.22 mm
V = 2662.8 (4) Å3

Bruker SMART APEX CCD area detector diffractometer	10273 independent reflections
Radiation source: fine-focus sealed tube	6679 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 193(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −12→15
Tmin = 0.848, Tmax = 0.879	k = −15→15
14596 measured reflections	l = −21→20

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
10273 reflections	Δρmax = 0.97 e Å−3
675 parameters	Δρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−0.14992 (18)	0.29242 (18)	0.19427 (14)	0.0413 (8)
C2	−0.2086 (2)	0.29890 (17)	0.12587 (12)	0.0528 (10)
H2	−0.1987	0.3532	0.0811	0.063*
C3	−0.28204 (19)	0.2243 (2)	0.12443 (12)	0.0400 (8)
H3	−0.3213	0.2286	0.0787	0.048*
C4	−0.29687 (19)	0.14321 (18)	0.19139 (14)	0.0448 (9)
H4	−0.3460	0.0933	0.1904	0.054*
C5	−0.2382 (2)	0.13673 (19)	0.25979 (12)	0.0525 (11)
H5	−0.2481	0.0825	0.3046	0.063*
C6	−0.1647 (2)	0.2113 (2)	0.26123 (12)	0.0533 (11)
H6	−0.1255	0.2070	0.3070	0.064*
C7	−0.0082 (3)	0.3575 (3)	0.2531 (2)	0.0420 (9)
H7A	0.0371	0.2911	0.2558	0.050*
H7B	−0.0486	0.3521	0.3032	0.050*
C8	0.0627 (3)	0.4501 (3)	0.24232 (19)	0.0309 (7)
C9	0.5655 (3)	0.5993 (3)	0.1346 (2)	0.0354 (7)
C10	0.6748 (3)	0.5765 (3)	0.1533 (2)	0.0393 (8)
H10	0.7077	0.5077	0.1560	0.047*
C11	0.7337 (3)	0.6559 (3)	0.1676 (2)	0.0408 (8)
H11	0.8064	0.6402	0.1792	0.049*
C12	0.6876 (3)	0.7566 (3)	0.1652 (2)	0.0445 (9)
H12	0.7288	0.8095	0.1741	0.053*
C13	0.5785 (3)	0.7801 (3)	0.1493 (2)	0.0399 (8)
H13	0.5458	0.8483	0.1490	0.048*
C14	0.5185 (3)	0.7011 (3)	0.1337 (2)	0.0442 (9)
H14	0.4457	0.7172	0.1226	0.053*
C15	0.4190 (3)	0.5449 (3)	0.0745 (2)	0.0389 (8)
H15A	0.4078	0.4873	0.0480	0.047*
H15B	0.4283	0.6086	0.0333	0.047*
C16	0.3174 (3)	0.5660 (3)	0.1243 (2)	0.0310 (7)
C17	0.3770 (3)	1.0392 (3)	0.1738 (2)	0.0393 (8)
C18	0.3870 (3)	1.0841 (3)	0.2409 (2)	0.0452 (9)
H18	0.3741	1.0449	0.2923	0.054*
C19	0.4157 (3)	1.1856 (3)	0.2287 (2)	0.0438 (9)
H19	0.4190	1.2166	0.2727	0.053*
C20	0.4399 (3)	1.2444 (3)	0.1549 (2)	0.0480 (10)
H20	0.4620	1.3130	0.1485	0.058*
C21	0.4307 (3)	1.1994 (4)	0.0907 (3)	0.0535 (11)
H21	0.4451	1.2389	0.0397	0.064*
C22	0.4008 (3)	1.0974 (4)	0.0996 (2)	0.0508 (10)
H22	0.3967	1.0678	0.0549	0.061*
C23	0.3286 (4)	0.8737 (3)	0.2547 (2)	0.0484 (11)
H23A	0.2800	0.9126	0.2862	0.058*
H23B	0.3969	0.8562	0.2819	0.058*
C24	0.2811 (3)	0.7703 (3)	0.2477 (2)	0.0335 (7)
C25	−0.1736 (4)	0.7864 (3)	0.4493 (2)	0.0498 (10)
C26	−0.2615 (3)	0.8525 (3)	0.4155 (3)	0.0514 (10)
H26	−0.2677	0.8709	0.3602	0.062*
C27	−0.3402 (3)	0.8912 (3)	0.4640 (2)	0.0439 (9)
H27	−0.3979	0.9374	0.4412	0.053*
C28	−0.3331 (3)	0.8612 (3)	0.5466 (2)	0.0410 (8)
H28	−0.3857	0.8874	0.5793	0.049*
C29	−0.2472 (3)	0.7921 (3)	0.5800 (2)	0.0440 (9)
H29	−0.2430	0.7708	0.6353	0.053*
C30	−0.1684 (3)	0.7548 (4)	0.5324 (2)	0.0461 (9)
H30	−0.1111	0.7082	0.5556	0.055*
C31	−0.0959 (3)	0.7740 (3)	0.3230 (2)	0.0464 (9)
H31A	−0.0951	0.8511	0.3061	0.056*
H31B	−0.1633	0.7544	0.3063	0.056*
C32	−0.0029 (3)	0.7204 (3)	0.28230 (19)	0.0360 (8)
C33	0.1833 (3)	0.9173 (3)	0.0287 (2)	0.0370 (8)
H33	0.2324	0.9084	0.0695	0.044*
C34	0.1832 (3)	1.0099 (3)	−0.0315 (2)	0.0450 (9)
H34	0.2307	1.0612	−0.0304	0.054*
C35	0.1116 (3)	1.0241 (3)	−0.0925 (2)	0.0446 (9)
H35	0.1099	1.0854	−0.1331	0.054*
C36	0.0412 (3)	0.9455 (3)	−0.0928 (2)	0.0389 (8)
C37	0.0465 (3)	0.8542 (3)	−0.02921 (19)	0.0313 (7)
C38	−0.0349 (3)	0.9524 (3)	−0.1547 (2)	0.0484 (10)
H38	−0.0397	1.0125	−0.1964	0.058*
C39	−0.0986 (3)	0.8749 (3)	−0.1535 (2)	0.0400 (9)
H39	−0.1480	0.8822	−0.1940	0.048*
C40	−0.0930 (3)	0.7803 (3)	−0.0912 (2)	0.0404 (9)
C41	−0.0215 (3)	0.7696 (3)	−0.0285 (2)	0.0341 (7)
C42	−0.1555 (3)	0.6923 (3)	−0.0897 (2)	0.0398 (8)
H42	−0.2046	0.6951	−0.1296	0.048*
C43	−0.1425 (3)	0.6043 (4)	−0.0292 (2)	0.0494 (10)
H43	−0.1804	0.5451	−0.0287	0.059*
C44	−0.0725 (3)	0.6034 (3)	0.0315 (2)	0.0420 (8)
H44	−0.0673	0.5439	0.0737	0.050*
C45	0.4660 (3)	0.4104 (3)	0.3261 (2)	0.0489 (10)
H45	0.4630	0.4243	0.2706	0.059*
C46	0.5584 (3)	0.3533 (4)	0.3622 (2)	0.0520 (11)
H46	0.6151	0.3290	0.3319	0.062*
C47	0.5625 (4)	0.3341 (3)	0.4441 (3)	0.0555 (12)
H47	0.6232	0.2966	0.4697	0.067*
C48	0.4771 (3)	0.3700 (3)	0.4897 (3)	0.0520 (11)
C49	0.4763 (3)	0.3541 (3)	0.5763 (3)	0.0514 (11)
H49	0.5364	0.3193	0.6042	0.062*
C50	0.3923 (3)	0.3878 (3)	0.6161 (2)	0.0427 (9)
H50	0.3940	0.3756	0.6715	0.051*
C51	0.2991 (3)	0.4425 (3)	0.5758 (2)	0.0429 (9)
C52	0.2071 (3)	0.4781 (3)	0.6160 (2)	0.0407 (9)
H52	0.2050	0.4660	0.6715	0.049*
C53	0.1195 (3)	0.5313 (3)	0.5726 (2)	0.0430 (9)
H53	0.0574	0.5537	0.5986	0.052*
C54	0.1259 (4)	0.5508 (4)	0.4887 (2)	0.0514 (10)
H54	0.0674	0.5879	0.4599	0.062*
C55	0.2979 (3)	0.4632 (3)	0.4909 (2)	0.0407 (9)
C56	0.3875 (3)	0.4251 (3)	0.4477 (2)	0.0396 (9)
C57	0.0849 (6)	0.9332 (6)	0.4635 (5)	0.0479 (19)	0.50
H57A	0.0356	0.9278	0.4233	0.072*	0.50
H57B	0.1132	1.0022	0.4502	0.072*	0.50
H57C	0.0478	0.9250	0.5144	0.072*	0.50
Mn1	0.10626 (4)	0.68940 (4)	0.13078 (3)	0.03282 (14)
Mn2	0.23017 (4)	0.55146 (4)	0.31185 (3)	0.03575 (15)
N1	0.1173 (2)	0.8407 (2)	0.03126 (18)	0.0357 (6)
N2	−0.0120 (2)	0.6833 (2)	0.03250 (16)	0.0330 (6)
N3	0.3823 (3)	0.4459 (2)	0.36634 (18)	0.0380 (7)
N4	0.2115 (3)	0.5187 (2)	0.44880 (17)	0.0392 (7)
O1	0.0482 (2)	0.5285 (2)	0.18646 (15)	0.0429 (6)
O2	0.1310 (2)	0.4354 (2)	0.29637 (15)	0.0419 (6)
O3	0.23937 (19)	0.6113 (2)	0.08234 (13)	0.0364 (5)
O4	0.3193 (2)	0.5381 (2)	0.19865 (14)	0.0407 (6)
O5	0.2302 (2)	0.7683 (2)	0.18841 (14)	0.0422 (6)
O6	0.2997 (2)	0.6956 (2)	0.30779 (14)	0.0421 (6)
O7	−0.0072 (2)	0.7512 (2)	0.20771 (14)	0.0419 (6)
O8	0.0669 (2)	0.6563 (2)	0.32082 (14)	0.0429 (6)
O9	−0.0808 (2)	0.3710 (2)	0.18956 (16)	0.0488 (7)
O10	0.5155 (2)	0.5172 (2)	0.11822 (17)	0.0502 (7)
O11	0.34476 (19)	0.93894 (19)	0.17765 (14)	0.0364 (5)
O12	−0.0909 (2)	0.7446 (2)	0.40745 (14)	0.0436 (6)
O13	0.1737 (5)	0.8490 (6)	0.4676 (4)	0.0653 (17)	0.50
H13A	0.1493	0.7918	0.4678	0.098*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0321 (18)	0.047 (2)	0.048 (2)	−0.0083 (16)	0.0017 (16)	−0.0154 (17)
C2	0.039 (2)	0.064 (3)	0.059 (3)	−0.0034 (19)	−0.0030 (19)	−0.020 (2)
C3	0.041 (2)	0.047 (2)	0.0373 (19)	−0.0152 (16)	−0.0023 (16)	−0.0153 (16)
C4	0.052 (2)	0.048 (2)	0.040 (2)	−0.0109 (18)	0.0000 (17)	−0.0187 (17)
C5	0.047 (2)	0.069 (3)	0.041 (2)	−0.036 (2)	0.0106 (18)	−0.0006 (19)
C6	0.054 (2)	0.063 (3)	0.042 (2)	−0.028 (2)	−0.0052 (19)	−0.0007 (19)
C7	0.046 (2)	0.040 (2)	0.038 (2)	−0.0128 (17)	−0.0056 (16)	−0.0006 (16)
C8	0.0352 (18)	0.0359 (18)	0.0220 (16)	−0.0106 (14)	0.0027 (13)	−0.0045 (13)
C9	0.0341 (18)	0.0407 (19)	0.0306 (18)	−0.0041 (14)	0.0080 (14)	−0.0066 (14)
C10	0.0315 (18)	0.041 (2)	0.043 (2)	0.0055 (15)	0.0025 (15)	−0.0088 (16)
C11	0.0355 (19)	0.055 (2)	0.0354 (19)	−0.0203 (17)	0.0029 (15)	−0.0103 (16)
C12	0.043 (2)	0.039 (2)	0.051 (2)	−0.0162 (17)	0.0105 (18)	−0.0062 (17)
C13	0.040 (2)	0.0389 (19)	0.0410 (19)	−0.0214 (15)	0.0001 (15)	−0.0022 (15)
C14	0.041 (2)	0.052 (2)	0.036 (2)	−0.0127 (17)	0.0000 (16)	0.0011 (17)
C15	0.046 (2)	0.0366 (19)	0.0373 (19)	−0.0051 (15)	0.0008 (16)	−0.0141 (15)
C16	0.0316 (17)	0.0262 (16)	0.0341 (19)	−0.0034 (13)	−0.0061 (14)	−0.0027 (13)
C17	0.0369 (19)	0.0340 (19)	0.046 (2)	−0.0066 (14)	−0.0044 (16)	−0.0050 (15)
C18	0.044 (2)	0.048 (2)	0.051 (2)	−0.0303 (18)	0.0025 (18)	−0.0148 (18)
C19	0.0401 (19)	0.055 (2)	0.050 (2)	−0.0270 (17)	0.0058 (16)	−0.0336 (19)
C20	0.063 (3)	0.035 (2)	0.045 (2)	−0.0208 (18)	0.0022 (19)	−0.0008 (16)
C21	0.040 (2)	0.060 (3)	0.052 (2)	−0.0241 (19)	−0.0029 (18)	0.014 (2)
C22	0.054 (2)	0.058 (3)	0.042 (2)	−0.022 (2)	0.0002 (18)	−0.0060 (18)
C23	0.078 (3)	0.035 (2)	0.0332 (19)	−0.0255 (19)	−0.0205 (19)	0.0022 (15)
C24	0.0406 (19)	0.0219 (16)	0.0368 (19)	−0.0077 (13)	−0.0052 (15)	−0.0008 (14)
C25	0.057 (2)	0.049 (2)	0.042 (2)	−0.0091 (19)	0.0114 (18)	−0.0055 (17)
C26	0.050 (2)	0.041 (2)	0.058 (3)	0.0090 (18)	0.0098 (19)	−0.0052 (18)
C27	0.041 (2)	0.042 (2)	0.046 (2)	0.0180 (16)	0.0153 (17)	−0.0147 (17)
C28	0.043 (2)	0.042 (2)	0.039 (2)	−0.0013 (16)	0.0110 (16)	−0.0127 (16)
C29	0.047 (2)	0.045 (2)	0.043 (2)	−0.0116 (17)	0.0154 (17)	−0.0158 (17)
C30	0.038 (2)	0.064 (3)	0.038 (2)	−0.0127 (18)	0.0077 (16)	−0.0131 (18)
C31	0.049 (2)	0.050 (2)	0.038 (2)	−0.0007 (18)	0.0033 (17)	−0.0077 (17)
C32	0.047 (2)	0.0372 (19)	0.0220 (16)	−0.0050 (15)	−0.0011 (14)	−0.0018 (14)
C33	0.0399 (19)	0.0396 (19)	0.0289 (17)	−0.0075 (15)	−0.0081 (14)	0.0014 (14)
C34	0.047 (2)	0.041 (2)	0.042 (2)	−0.0131 (17)	−0.0026 (17)	0.0049 (16)
C35	0.047 (2)	0.044 (2)	0.035 (2)	−0.0064 (17)	−0.0016 (17)	0.0102 (16)
C36	0.046 (2)	0.040 (2)	0.0242 (17)	0.0077 (16)	−0.0019 (15)	0.0005 (14)
C37	0.0304 (17)	0.0383 (18)	0.0235 (16)	0.0053 (14)	0.0006 (13)	−0.0070 (13)
C38	0.054 (2)	0.050 (2)	0.034 (2)	0.0077 (19)	−0.0127 (17)	0.0049 (17)
C39	0.042 (2)	0.044 (2)	0.0320 (18)	0.0144 (17)	−0.0149 (15)	−0.0081 (15)
C40	0.0336 (18)	0.060 (2)	0.0252 (17)	0.0065 (17)	−0.0031 (14)	−0.0077 (16)
C41	0.0268 (16)	0.0376 (19)	0.0351 (18)	−0.0027 (13)	−0.0019 (13)	−0.0017 (14)
C42	0.0388 (19)	0.048 (2)	0.041 (2)	−0.0062 (16)	−0.0086 (16)	−0.0249 (17)
C43	0.044 (2)	0.062 (3)	0.044 (2)	−0.0156 (19)	−0.0107 (18)	−0.0097 (19)
C44	0.043 (2)	0.052 (2)	0.0322 (19)	−0.0139 (17)	−0.0020 (16)	−0.0065 (16)
C45	0.058 (3)	0.045 (2)	0.045 (2)	−0.0003 (19)	−0.022 (2)	−0.0084 (18)
C46	0.052 (2)	0.061 (3)	0.044 (2)	0.008 (2)	−0.0162 (19)	−0.015 (2)
C47	0.061 (3)	0.045 (2)	0.059 (3)	−0.0033 (19)	−0.044 (2)	0.0002 (19)
C48	0.049 (2)	0.041 (2)	0.063 (3)	−0.0059 (18)	−0.028 (2)	0.0015 (19)
C49	0.033 (2)	0.053 (2)	0.060 (3)	−0.0105 (17)	−0.0170 (19)	0.011 (2)
C50	0.036 (2)	0.044 (2)	0.041 (2)	−0.0145 (16)	−0.0165 (16)	0.0147 (16)
C51	0.045 (2)	0.047 (2)	0.0339 (19)	−0.0225 (17)	−0.0198 (16)	0.0090 (16)
C52	0.040 (2)	0.043 (2)	0.039 (2)	−0.0278 (16)	−0.0008 (16)	0.0012 (16)
C53	0.051 (2)	0.042 (2)	0.037 (2)	−0.0132 (17)	−0.0002 (17)	−0.0077 (16)
C54	0.058 (3)	0.062 (3)	0.0269 (19)	−0.006 (2)	−0.0062 (17)	0.0067 (17)
C55	0.048 (2)	0.0348 (18)	0.0367 (19)	−0.0167 (16)	−0.0159 (16)	0.0060 (15)
C56	0.053 (2)	0.0313 (18)	0.0329 (18)	−0.0128 (16)	−0.0225 (17)	0.0052 (14)
C57	0.035 (4)	0.043 (4)	0.055 (5)	−0.009 (3)	−0.008 (3)	0.016 (3)
Mn1	0.0289 (3)	0.0314 (3)	0.0355 (3)	−0.0038 (2)	−0.0041 (2)	0.0000 (2)
Mn2	0.0364 (3)	0.0314 (3)	0.0366 (3)	−0.0078 (2)	−0.0083 (2)	0.0024 (2)
N1	0.0320 (15)	0.0337 (15)	0.0381 (16)	0.0000 (12)	−0.0022 (12)	−0.0015 (12)
N2	0.0281 (14)	0.0394 (16)	0.0318 (15)	−0.0061 (12)	−0.0016 (12)	−0.0064 (12)
N3	0.0462 (17)	0.0304 (15)	0.0382 (16)	−0.0065 (13)	−0.0141 (14)	−0.0050 (12)
N4	0.0487 (18)	0.0388 (17)	0.0282 (15)	−0.0106 (14)	−0.0076 (13)	0.0009 (12)
O1	0.0521 (15)	0.0384 (14)	0.0366 (14)	−0.0138 (12)	−0.0076 (12)	0.0012 (11)
O2	0.0519 (15)	0.0366 (14)	0.0357 (13)	−0.0156 (11)	−0.0117 (12)	0.0026 (10)
O3	0.0327 (12)	0.0483 (15)	0.0283 (12)	0.0008 (11)	−0.0049 (10)	−0.0093 (10)
O4	0.0439 (14)	0.0495 (15)	0.0262 (13)	0.0004 (11)	−0.0043 (10)	−0.0038 (11)
O5	0.0565 (16)	0.0384 (14)	0.0318 (13)	−0.0130 (12)	−0.0175 (12)	−0.0012 (10)
O6	0.0509 (15)	0.0380 (14)	0.0333 (13)	−0.0109 (11)	−0.0137 (11)	0.0066 (11)
O7	0.0435 (14)	0.0519 (16)	0.0258 (13)	0.0047 (12)	−0.0031 (10)	−0.0016 (11)
O8	0.0459 (15)	0.0510 (16)	0.0263 (12)	0.0064 (12)	−0.0057 (11)	0.0000 (11)
O9	0.0467 (15)	0.0524 (16)	0.0472 (16)	−0.0239 (13)	−0.0109 (12)	−0.0003 (12)
O10	0.0340 (14)	0.0604 (18)	0.0550 (17)	0.0028 (12)	−0.0024 (12)	−0.0129 (14)
O11	0.0392 (13)	0.0359 (13)	0.0351 (13)	−0.0214 (10)	−0.0053 (10)	−0.0017 (10)
O12	0.0621 (17)	0.0379 (14)	0.0248 (12)	0.0096 (12)	0.0077 (11)	−0.0011 (10)
O13	0.055 (4)	0.069 (4)	0.077 (5)	−0.015 (3)	0.019 (3)	−0.026 (4)

C1—O9	1.374 (3)	C31—H31B	0.9700
C1—C2	1.3900	C32—O8	1.243 (4)
C1—C6	1.3900	C32—O7	1.255 (4)
C2—C3	1.3900	C33—N1	1.332 (5)
C2—H2	0.9300	C33—C34	1.394 (5)
C3—C4	1.3900	C33—H33	0.9300
C3—H3	0.9300	C34—C35	1.372 (5)
C4—C5	1.3900	C34—H34	0.9300
C4—H4	0.9300	C35—C36	1.399 (6)
C5—C6	1.3900	C35—H35	0.9300
C5—H5	0.9300	C36—C37	1.415 (5)
C6—H6	0.9300	C36—C38	1.434 (5)
C7—O9	1.415 (4)	C37—N1	1.361 (4)
C7—C8	1.521 (5)	C37—C41	1.436 (5)
C7—H7A	0.9700	C38—C39	1.327 (6)
C7—H7B	0.9700	C38—H38	0.9300
C8—O1	1.234 (4)	C39—C40	1.429 (5)
C8—O2	1.256 (4)	C39—H39	0.9300
C9—O10	1.358 (5)	C40—C41	1.400 (5)
C9—C14	1.378 (5)	C40—C42	1.425 (5)
C9—C10	1.402 (5)	C41—N2	1.347 (4)
C10—C11	1.379 (5)	C42—C43	1.358 (6)
C10—H10	0.9300	C42—H42	0.9300
C11—C12	1.356 (5)	C43—C44	1.382 (5)
C11—H11	0.9300	C43—H43	0.9300
C12—C13	1.390 (5)	C44—N2	1.332 (5)
C12—H12	0.9300	C44—H44	0.9300
C13—C14	1.391 (5)	C45—N3	1.327 (5)
C13—H13	0.9300	C45—C46	1.396 (5)
C14—H14	0.9300	C45—H45	0.9300
C15—O10	1.418 (4)	C46—C47	1.374 (6)
C15—C16	1.533 (5)	C46—H46	0.9300
C15—H15A	0.9700	C47—C48	1.397 (7)
C15—H15B	0.9700	C47—H47	0.9300
C16—O4	1.247 (4)	C48—C56	1.401 (5)
C16—O3	1.254 (4)	C48—C49	1.452 (6)
C17—C22	1.364 (6)	C49—C50	1.315 (6)
C17—O11	1.371 (4)	C49—H49	0.9300
C17—C18	1.408 (5)	C50—C51	1.422 (5)
C18—C19	1.354 (5)	C50—H50	0.9300
C18—H18	0.9300	C51—C52	1.405 (6)
C19—C20	1.364 (6)	C51—C55	1.421 (5)
C19—H19	0.9300	C52—C53	1.385 (5)
C20—C21	1.361 (6)	C52—H52	0.9300
C20—H20	0.9300	C53—C54	1.405 (5)
C21—C22	1.369 (6)	C53—H53	0.9300
C21—H21	0.9300	C54—N4	1.324 (5)
C22—H22	0.9300	C54—H54	0.9300
C23—O11	1.419 (4)	C55—N4	1.373 (5)
C23—C24	1.532 (5)	C55—C56	1.421 (6)
C23—H23A	0.9700	C56—N3	1.365 (5)
C23—H23B	0.9700	C57—O13	1.465 (10)
C24—O5	1.227 (4)	C57—H57A	0.9600
C24—O6	1.257 (4)	C57—H57B	0.9600
C25—O12	1.366 (5)	C57—H57C	0.9600
C25—C26	1.385 (6)	Mn1—O1	2.250 (3)
C25—C30	1.397 (6)	Mn1—O3	2.094 (2)
C26—C27	1.386 (5)	Mn1—O5	2.289 (2)
C26—H26	0.9300	Mn1—O7	2.112 (3)
C27—C28	1.388 (5)	Mn1—N1	2.299 (3)
C27—H27	0.9300	Mn1—N2	2.302 (3)
C28—C29	1.382 (6)	Mn2—O2	2.087 (2)
C28—H28	0.9300	Mn2—O4	2.227 (3)
C29—C30	1.369 (5)	Mn2—O6	2.102 (2)
C29—H29	0.9300	Mn2—O8	2.351 (3)
C30—H30	0.9300	Mn2—N3	2.327 (3)
C31—O12	1.417 (4)	Mn2—N4	2.299 (3)
C31—C32	1.515 (5)	O13—H13A	0.8200
C31—H31A	0.9700
O9—C1—C2	115.15 (19)	N1—C37—C41	117.6 (3)
O9—C1—C6	124.84 (19)	C36—C37—C41	120.0 (3)
C2—C1—C6	120.0	C39—C38—C36	121.3 (4)
C3—C2—C1	120.0	C39—C38—H38	119.3
C3—C2—H2	120.0	C36—C38—H38	119.3
C1—C2—H2	120.0	C38—C39—C40	121.4 (3)
C2—C3—C4	120.0	C38—C39—H39	119.3
C2—C3—H3	120.0	C40—C39—H39	119.3
C4—C3—H3	120.0	C41—C40—C42	116.6 (3)
C3—C4—C5	120.0	C41—C40—C39	120.0 (4)
C3—C4—H4	120.0	C42—C40—C39	123.4 (3)
C5—C4—H4	120.0	N2—C41—C40	123.4 (3)
C6—C5—C4	120.0	N2—C41—C37	117.9 (3)
C6—C5—H5	120.0	C40—C41—C37	118.7 (3)
C4—C5—H5	120.0	C43—C42—C40	119.3 (3)
C5—C6—C1	120.0	C43—C42—H42	120.4
C5—C6—H6	120.0	C40—C42—H42	120.4
C1—C6—H6	120.0	C42—C43—C44	119.6 (4)
O9—C7—C8	111.8 (3)	C42—C43—H43	120.2
O9—C7—H7A	109.3	C44—C43—H43	120.2
C8—C7—H7A	109.3	N2—C44—C43	123.3 (4)
O9—C7—H7B	109.3	N2—C44—H44	118.3
C8—C7—H7B	109.3	C43—C44—H44	118.3
H7A—C7—H7B	107.9	N3—C45—C46	123.8 (4)
O1—C8—O2	127.6 (3)	N3—C45—H45	118.1
O1—C8—C7	120.6 (3)	C46—C45—H45	118.1
O2—C8—C7	111.9 (3)	C47—C46—C45	117.6 (4)
O10—C9—C14	125.8 (3)	C47—C46—H46	121.2
O10—C9—C10	115.7 (3)	C45—C46—H46	121.2
C14—C9—C10	118.4 (3)	C46—C47—C48	121.3 (4)
C11—C10—C9	120.0 (3)	C46—C47—H47	119.4
C11—C10—H10	120.0	C48—C47—H47	119.4
C9—C10—H10	120.0	C47—C48—C56	116.6 (4)
C12—C11—C10	121.3 (4)	C47—C48—C49	124.4 (4)
C12—C11—H11	119.3	C56—C48—C49	119.0 (4)
C10—C11—H11	119.3	C50—C49—C48	121.5 (4)
C11—C12—C13	119.6 (3)	C50—C49—H49	119.2
C11—C12—H12	120.2	C48—C49—H49	119.2
C13—C12—H12	120.2	C49—C50—C51	121.2 (4)
C12—C13—C14	119.7 (4)	C49—C50—H50	119.4
C12—C13—H13	120.2	C51—C50—H50	119.4
C14—C13—H13	120.2	C52—C51—C55	117.8 (3)
C9—C14—C13	120.9 (4)	C52—C51—C50	123.0 (3)
C9—C14—H14	119.6	C55—C51—C50	119.2 (4)
C13—C14—H14	119.6	C53—C52—C51	119.7 (3)
O10—C15—C16	115.2 (3)	C53—C52—H52	120.1
O10—C15—H15A	108.5	C51—C52—H52	120.1
C16—C15—H15A	108.5	C52—C53—C54	118.9 (4)
O10—C15—H15B	108.5	C52—C53—H53	120.6
C16—C15—H15B	108.5	C54—C53—H53	120.6
H15A—C15—H15B	107.5	N4—C54—C53	123.0 (4)
O4—C16—O3	127.3 (3)	N4—C54—H54	118.5
O4—C16—C15	119.7 (3)	C53—C54—H54	118.5
O3—C16—C15	113.0 (3)	N4—C55—C56	118.6 (3)
C22—C17—O11	116.7 (3)	N4—C55—C51	121.6 (4)
C22—C17—C18	119.2 (4)	C56—C55—C51	119.8 (3)
O11—C17—C18	124.1 (3)	N3—C56—C48	123.1 (4)
C19—C18—C17	118.3 (4)	N3—C56—C55	117.7 (3)
C19—C18—H18	120.8	C48—C56—C55	119.2 (4)
C17—C18—H18	120.8	O13—C57—H57A	109.5
C18—C19—C20	122.9 (3)	O13—C57—H57B	109.5
C18—C19—H19	118.6	H57A—C57—H57B	109.5
C20—C19—H19	118.6	O13—C57—H57C	109.5
C21—C20—C19	117.9 (4)	H57A—C57—H57C	109.5
C21—C20—H20	121.1	H57B—C57—H57C	109.5
C19—C20—H20	121.1	O3—Mn1—O7	165.10 (9)
C20—C21—C22	121.6 (4)	O3—Mn1—O1	89.02 (10)
C20—C21—H21	119.2	O7—Mn1—O1	85.90 (10)
C22—C21—H21	119.2	O3—Mn1—O5	85.75 (10)
C17—C22—C21	120.0 (4)	O7—Mn1—O5	85.38 (10)
C17—C22—H22	120.0	O1—Mn1—O5	123.41 (9)
C21—C22—H22	120.0	O3—Mn1—N1	91.36 (10)
O11—C23—C24	110.2 (3)	O7—Mn1—N1	99.24 (10)
O11—C23—H23A	109.6	O1—Mn1—N1	154.47 (10)
C24—C23—H23A	109.6	O5—Mn1—N1	82.06 (9)
O11—C23—H23B	109.6	O3—Mn1—N2	96.27 (9)
C24—C23—H23B	109.6	O7—Mn1—N2	96.98 (10)
H23A—C23—H23B	108.1	O1—Mn1—N2	82.86 (10)
O5—C24—O6	127.7 (3)	O5—Mn1—N2	153.72 (10)
O5—C24—C23	119.8 (3)	N1—Mn1—N2	71.72 (10)
O6—C24—C23	112.5 (3)	O2—Mn2—O6	164.69 (10)
O12—C25—C26	125.1 (4)	O2—Mn2—O4	90.14 (10)
O12—C25—C30	115.6 (4)	O6—Mn2—O4	88.70 (10)
C26—C25—C30	119.2 (4)	O2—Mn2—N4	95.76 (10)
C25—C26—C27	120.1 (4)	O6—Mn2—N4	92.14 (10)
C25—C26—H26	120.0	O4—Mn2—N4	153.09 (11)
C27—C26—H26	120.0	O2—Mn2—N3	101.55 (10)
C26—C27—C28	120.2 (4)	O6—Mn2—N3	93.36 (10)
C26—C27—H27	119.9	O4—Mn2—N3	81.30 (10)
C28—C27—H27	119.9	N4—Mn2—N3	71.79 (11)
C29—C28—C27	119.4 (3)	O2—Mn2—O8	84.33 (10)
C29—C28—H28	120.3	O6—Mn2—O8	83.89 (10)
C27—C28—H28	120.3	O4—Mn2—O8	125.25 (9)
C30—C29—C28	120.7 (4)	N4—Mn2—O8	81.54 (10)
C30—C29—H29	119.6	N3—Mn2—O8	153.09 (10)
C28—C29—H29	119.6	C33—N1—C37	117.5 (3)
C29—C30—C25	120.3 (4)	C33—N1—Mn1	126.4 (2)
C29—C30—H30	119.9	C37—N1—Mn1	116.1 (2)
C25—C30—H30	119.9	C44—N2—C41	117.7 (3)
O12—C31—C32	112.3 (3)	C44—N2—Mn1	125.9 (2)
O12—C31—H31A	109.1	C41—N2—Mn1	116.4 (2)
C32—C31—H31A	109.1	C45—N3—C56	117.7 (3)
O12—C31—H31B	109.1	C45—N3—Mn2	126.5 (2)
C32—C31—H31B	109.1	C56—N3—Mn2	115.7 (3)
H31A—C31—H31B	107.9	C54—N4—C55	118.9 (3)
O8—C32—O7	127.1 (3)	C54—N4—Mn2	125.1 (2)
O8—C32—C31	122.1 (3)	C55—N4—Mn2	116.0 (3)
O7—C32—C31	110.8 (3)	C8—O1—Mn1	143.6 (2)
N1—C33—C34	123.9 (3)	C8—O2—Mn2	123.9 (2)
N1—C33—H33	118.0	C16—O3—Mn1	121.8 (2)
C34—C33—H33	118.0	C16—O4—Mn2	144.6 (2)
C35—C34—C33	118.8 (4)	C24—O5—Mn1	148.5 (2)
C35—C34—H34	120.6	C24—O6—Mn2	117.4 (2)
C33—C34—H34	120.6	C32—O7—Mn1	121.6 (2)
C34—C35—C36	119.4 (3)	C32—O8—Mn2	145.0 (2)
C34—C35—H35	120.3	C1—O9—C7	116.4 (3)
C36—C35—H35	120.3	C9—O10—C15	116.7 (3)
C35—C36—C37	118.0 (3)	C17—O11—C23	117.4 (3)
C35—C36—C38	123.4 (3)	C25—O12—C31	116.4 (3)
C37—C36—C38	118.6 (4)	C57—O13—H13A	109.5
N1—C37—C36	122.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O10i	0.93	2.70	3.627 (5)	175

Table 1

Selected bond lengths (Å)

Mn1—O1	2.250 (3)
Mn1—O3	2.094 (2)
Mn1—O5	2.289 (2)
Mn1—O7	2.112 (3)
Mn1—N1	2.299 (3)
Mn1—N2	2.302 (3)
Mn2—O2	2.087 (2)
Mn2—O4	2.227 (3)
Mn2—O6	2.102 (2)
Mn2—O8	2.351 (3)
Mn2—N3	2.327 (3)
Mn2—N4	2.299 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O10i	0.93	2.70	3.627 (5)	175

Symmetry code: (i) .