Diaqua-bis-(5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O)manganese(II) 3.5-hydrate.

In the title complex, [Mn(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·3.5H(2)O, the Mn(II) cation is six-coordinated by two N,O-bidentate H(2)pimda(-) ligands (H(2)pimda(-) = 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate) and two water mol-ecules in a distorted octa-hedral environment. The complete solid-state structure can be described as a three-dimensional supra-molecular framework stabilized by a wide range of O-H⋯O and N-H⋯O hydrogen bonds. The propyl groups of H(2)pimda(-) are disordered over two sets of sites with refined occupancies of 0.759 (5):0.241 (5) and 0.545 (7):0.455 (7).

Related literature

For our previous structural studies of complexes with H2pimda−, see: Yan et al. (2010 ▶); Li et al. (2010 ▶); Song et al.(2010 ▶); He et al. (2010 ▶); Fan et al. (2010 ▶).

Experimental

Crystal data

[Mn(C8H9N2O4)2(H2O)2]·3.5H2O

M = 548.37

Triclinic,

a = 10.609 (6) Å

b = 10.649 (6) Å

c = 11.424 (7) Å

α = 82.748 (8)°

β = 82.544 (7)°

γ = 86.857 (7)°

V = 1268.5 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.59 mm−1

T = 296 K

0.31 × 0.26 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.838, T max = 0.886

6656 measured reflections

4508 independent reflections

2551 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.152

S = 1.00

4508 reflections

342 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031612/jh2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031612/jh2190Isup2.hkl

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

[Mn(C8H9N2O4)2(H2O)2]·3.5H2O	Z = 2
Mr = 548.37	F(000) = 572
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.609 (6) Å	Cell parameters from 3600 reflections
b = 10.649 (6) Å	θ = 1.4–25.0°
c = 11.424 (7) Å	µ = 0.59 mm−1
α = 82.748 (8)°	T = 296 K
β = 82.544 (7)°	Block, colorless
γ = 86.857 (7)°	0.31 × 0.26 × 0.21 mm
V = 1268.5 (13) Å3

Bruker APEXII area-detector diffractometer	4508 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scan	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.838, Tmax = 0.886	k = −12→12
6656 measured reflections	l = −13→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2346P] where P = (Fo2 + 2Fc2)/3
4508 reflections	(Δ/σ)max = 0.009
342 parameters	Δρmax = 0.32 e Å−3
5 restraints	Δρmin = −0.33 e Å−3

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	Occ. (<1)
Mn1	0.84879 (6)	0.29330 (6)	0.19294 (6)	0.0505 (2)
O1	0.8746 (4)	−0.1883 (3)	0.5157 (3)	0.0718 (10)
H1	0.8701	−0.1626	0.4455	0.108*
O2	0.8374 (3)	−0.1110 (3)	0.6882 (3)	0.0724 (10)
O3	0.8872 (3)	0.0868 (3)	0.1898 (3)	0.0582 (8)
O4	0.8969 (3)	−0.1020 (3)	0.2997 (3)	0.0662 (9)
O5	0.7711 (3)	0.4910 (3)	0.2083 (3)	0.0564 (8)
O6	0.6057 (3)	0.6263 (3)	0.1848 (3)	0.0691 (10)
O7	0.3863 (3)	0.6187 (3)	0.1382 (3)	0.0641 (9)
H6	0.4581	0.6182	0.1577	0.096*
O8	0.2555 (3)	0.4775 (3)	0.0983 (3)	0.0642 (9)
N1	0.8290 (3)	0.2105 (3)	0.3841 (3)	0.0500 (9)
N2	0.8112 (3)	0.1375 (4)	0.5753 (3)	0.0585 (10)
H2	0.7991	0.1451	0.6516	0.070*
N3	0.6401 (3)	0.2898 (3)	0.1720 (3)	0.0460 (9)
N4	0.4436 (3)	0.2822 (3)	0.1290 (3)	0.0505 (9)
H4	0.3776	0.2468	0.1111	0.061*
C1	0.8355 (4)	0.0337 (4)	0.5152 (4)	0.0440 (10)
C2	0.8473 (3)	0.0802 (4)	0.3970 (4)	0.0419 (10)
C3	0.8087 (5)	0.2420 (4)	0.4943 (4)	0.0604 (13)
C4	0.8790 (4)	0.0165 (4)	0.2877 (4)	0.0496 (11)
C5	0.8483 (4)	−0.0942 (5)	0.5799 (5)	0.0554 (12)
C6A	0.7996 (11)	0.3774 (11)	0.5220 (13)	0.084 (3)	0.759 (5)
H6A	0.8314	0.3810	0.5973	0.100*	0.759 (5)
H6B	0.8528	0.4288	0.4608	0.100*	0.759 (5)
C7A	0.6680 (8)	0.4301 (7)	0.5284 (8)	0.100 (3)	0.759 (5)
H7A	0.6169	0.3863	0.5964	0.120*	0.759 (5)
H7B	0.6321	0.4168	0.4573	0.120*	0.759 (5)
C8A	0.6635 (9)	0.5741 (7)	0.5402 (9)	0.137 (4)	0.759 (5)
H8A	0.5779	0.6013	0.5665	0.206*	0.759 (5)
H8B	0.6914	0.6202	0.4643	0.206*	0.759 (5)
H8C	0.7183	0.5897	0.5969	0.206*	0.759 (5)
C6B	0.747 (4)	0.358 (4)	0.541 (5)	0.084 (3)	0.241 (5)
H6C	0.6822	0.3936	0.4932	0.100*	0.241 (5)
H6D	0.7079	0.3376	0.6224	0.100*	0.241 (5)
C7B	0.846 (2)	0.452 (3)	0.538 (2)	0.100 (3)	0.241 (5)
H7C	0.8067	0.5350	0.5479	0.120*	0.241 (5)
H7D	0.8990	0.4584	0.4612	0.120*	0.241 (5)
C8B	0.929 (3)	0.410 (2)	0.638 (3)	0.137 (4)	0.241 (5)
H8D	0.9855	0.4767	0.6433	0.206*	0.241 (5)
H8E	0.9788	0.3351	0.6207	0.206*	0.241 (5)
H8F	0.8759	0.3933	0.7120	0.206*	0.241 (5)
C9	0.5827 (4)	0.4087 (4)	0.1688 (4)	0.0412 (10)
C10	0.4601 (4)	0.4059 (4)	0.1419 (4)	0.0432 (10)
C11	0.5528 (4)	0.2139 (4)	0.1468 (4)	0.0515 (11)
C12	0.6575 (4)	0.5144 (4)	0.1884 (4)	0.0507 (11)
C13	0.3590 (4)	0.5048 (4)	0.1255 (4)	0.0526 (12)
C14A	0.559 (3)	0.0724 (6)	0.1680 (13)	0.061 (3)	0.545 (7)
H14A	0.6447	0.0413	0.1436	0.073*	0.545 (7)
H14B	0.5023	0.0391	0.1202	0.073*	0.545 (7)
C15A	0.5196 (17)	0.0242 (9)	0.3025 (12)	0.093 (4)	0.545 (7)
H15A	0.5725	0.0607	0.3516	0.111*	0.545 (7)
H15B	0.4315	0.0488	0.3263	0.111*	0.545 (7)
C16A	0.5371 (12)	−0.1179 (9)	0.3172 (12)	0.107 (4)	0.545 (7)
H16A	0.5074	−0.1508	0.3976	0.160*	0.545 (7)
H16B	0.6257	−0.1410	0.2996	0.160*	0.545 (7)
H16C	0.4894	−0.1524	0.2637	0.160*	0.545 (7)
C14B	0.578 (3)	0.0799 (8)	0.1201 (18)	0.061 (3)	0.455 (7)
H14C	0.6668	0.0560	0.1241	0.073*	0.455 (7)
H14D	0.5594	0.0731	0.0402	0.073*	0.455 (7)
C15B	0.4928 (12)	−0.0126 (12)	0.2116 (12)	0.093 (4)	0.455 (7)
H15C	0.4039	0.0123	0.2083	0.111*	0.455 (7)
H15D	0.5061	−0.0979	0.1897	0.111*	0.455 (7)
C16B	0.523 (2)	−0.0117 (16)	0.3355 (14)	0.107 (4)	0.455 (7)
H16D	0.5291	−0.0971	0.3736	0.160*	0.455 (7)
H16E	0.4576	0.0352	0.3793	0.160*	0.455 (7)
H16F	0.6032	0.0274	0.3332	0.160*	0.455 (7)
O1W	0.8931 (3)	0.3345 (3)	0.0048 (3)	0.0828 (11)
H1W	0.9099	0.2672	−0.0280	0.124*
H2W	0.8568	0.3968	−0.0336	0.124*
O2W	1.0434 (3)	0.3326 (3)	0.2140 (3)	0.0849 (12)
H3W	1.0867	0.3943	0.1787	0.127*
H4W	1.0929	0.2699	0.2328	0.127*
O3W	0.9127 (6)	0.0143 (5)	0.9610 (5)	0.0656 (17)	0.50
H5W	0.9930	0.0018	0.9532	0.098*	0.50
H6W	0.9068	0.0143	1.0364	0.098*	0.50
O4W	0.7778 (4)	0.1620 (4)	0.8153 (4)	0.1275 (17)
H7W	0.8316	0.1163	0.8523	0.191*
H8W	0.7326	0.2287	0.8273	0.191*
O5W	0.1048 (3)	0.2730 (3)	0.8677 (3)	0.0828 (11)
H9W	0.1543	0.3290	0.8309	0.124*
H10W	0.1101	0.2120	0.8256	0.124*
O6W	0.2622 (3)	0.1565 (4)	0.0418 (4)	0.1110 (15)
H11W	0.2152	0.0928	0.0546	0.167*
H12W	0.2063	0.2152	0.0292	0.167*

	U11	U22	U33	U12	U13	U23
Mn1	0.0448 (4)	0.0542 (5)	0.0498 (5)	0.0021 (3)	−0.0097 (3)	0.0064 (3)
O1	0.091 (2)	0.051 (2)	0.071 (3)	0.0000 (18)	−0.019 (2)	0.0070 (18)
O2	0.073 (2)	0.082 (2)	0.052 (2)	0.0119 (18)	−0.0074 (18)	0.0235 (18)
O3	0.065 (2)	0.062 (2)	0.044 (2)	0.0122 (16)	−0.0093 (16)	0.0003 (16)
O4	0.094 (2)	0.049 (2)	0.058 (2)	0.0116 (17)	−0.0190 (18)	−0.0090 (16)
O5	0.0510 (18)	0.0522 (19)	0.068 (2)	−0.0029 (14)	−0.0201 (16)	−0.0028 (16)
O6	0.064 (2)	0.050 (2)	0.096 (3)	0.0058 (16)	−0.0150 (19)	−0.0153 (18)
O7	0.0532 (19)	0.057 (2)	0.081 (3)	0.0147 (16)	−0.0147 (18)	−0.0039 (18)
O8	0.0415 (17)	0.072 (2)	0.074 (2)	0.0008 (16)	−0.0118 (16)	0.0119 (17)
N1	0.051 (2)	0.054 (2)	0.043 (2)	0.0040 (17)	−0.0077 (18)	−0.0020 (18)
N2	0.063 (2)	0.070 (3)	0.041 (2)	0.007 (2)	−0.0037 (19)	−0.008 (2)
N3	0.046 (2)	0.040 (2)	0.051 (2)	0.0014 (16)	−0.0115 (17)	0.0029 (16)
N4	0.0364 (19)	0.053 (2)	0.061 (3)	−0.0019 (17)	−0.0159 (17)	0.0055 (18)
C1	0.040 (2)	0.048 (3)	0.043 (3)	0.0023 (19)	−0.005 (2)	0.000 (2)
C2	0.039 (2)	0.042 (2)	0.044 (3)	0.0022 (18)	−0.008 (2)	−0.002 (2)
C3	0.078 (3)	0.053 (3)	0.049 (3)	0.005 (2)	−0.008 (3)	−0.004 (2)
C4	0.044 (2)	0.055 (3)	0.051 (3)	0.008 (2)	−0.013 (2)	−0.006 (2)
C5	0.047 (3)	0.061 (3)	0.055 (3)	−0.002 (2)	−0.013 (2)	0.010 (3)
C6A	0.125 (12)	0.063 (6)	0.060 (7)	0.014 (7)	−0.005 (8)	−0.013 (5)
C7A	0.122 (7)	0.068 (5)	0.106 (7)	0.015 (5)	−0.002 (5)	−0.013 (5)
C8A	0.177 (10)	0.076 (6)	0.154 (10)	0.023 (6)	0.001 (7)	−0.025 (6)
C6B	0.125 (12)	0.063 (6)	0.060 (7)	0.014 (7)	−0.005 (8)	−0.013 (5)
C7B	0.122 (7)	0.068 (5)	0.106 (7)	0.015 (5)	−0.002 (5)	−0.013 (5)
C8B	0.177 (10)	0.076 (6)	0.154 (10)	0.023 (6)	0.001 (7)	−0.025 (6)
C9	0.041 (2)	0.040 (2)	0.041 (3)	0.0010 (19)	−0.0066 (19)	0.0023 (19)
C10	0.043 (2)	0.041 (3)	0.042 (3)	0.0043 (19)	−0.0047 (19)	0.0032 (19)
C11	0.045 (2)	0.047 (3)	0.062 (3)	−0.002 (2)	−0.013 (2)	0.000 (2)
C12	0.054 (3)	0.046 (3)	0.052 (3)	−0.001 (2)	−0.007 (2)	−0.003 (2)
C13	0.047 (3)	0.057 (3)	0.048 (3)	0.002 (2)	0.001 (2)	0.008 (2)
C14A	0.058 (8)	0.042 (3)	0.082 (12)	0.002 (3)	−0.023 (10)	0.004 (4)
C15A	0.073 (6)	0.056 (6)	0.143 (12)	−0.005 (5)	−0.023 (7)	0.021 (6)
C16A	0.116 (8)	0.068 (6)	0.133 (9)	−0.005 (7)	−0.022 (7)	0.006 (7)
C14B	0.058 (8)	0.042 (3)	0.082 (12)	0.002 (3)	−0.023 (10)	0.004 (4)
C15B	0.073 (6)	0.056 (6)	0.143 (12)	−0.005 (5)	−0.023 (7)	0.021 (6)
C16B	0.116 (8)	0.068 (6)	0.133 (9)	−0.005 (7)	−0.022 (7)	0.006 (7)
O1W	0.078 (2)	0.097 (3)	0.060 (2)	0.036 (2)	−0.0015 (18)	0.0170 (19)
O2W	0.052 (2)	0.088 (3)	0.105 (3)	−0.0148 (18)	−0.0197 (19)	0.043 (2)
O3W	0.072 (4)	0.074 (4)	0.051 (4)	0.006 (3)	−0.013 (3)	−0.011 (3)
O4W	0.156 (4)	0.155 (4)	0.078 (3)	0.069 (3)	−0.035 (3)	−0.053 (3)
O5W	0.073 (2)	0.078 (2)	0.100 (3)	−0.0245 (19)	0.013 (2)	−0.035 (2)
O6W	0.099 (3)	0.108 (3)	0.144 (4)	0.006 (2)	−0.064 (3)	−0.038 (3)

Mn1—O1W	2.134 (3)	C6B—H6D	0.9700
Mn1—O2W	2.178 (3)	C7B—C8B	1.540 (13)
Mn1—O3	2.218 (3)	C7B—H7C	0.9700
Mn1—N1	2.237 (4)	C7B—H7D	0.9700
Mn1—O5	2.238 (3)	C8B—H8D	0.9600
Mn1—N3	2.260 (3)	C8B—H8E	0.9600
O1—C5	1.312 (5)	C8B—H8F	0.9600
O1—H1	0.8200	C9—C10	1.377 (5)
O2—C5	1.219 (5)	C9—C12	1.468 (6)
O3—C4	1.261 (5)	C10—C13	1.474 (5)
O4—C4	1.259 (5)	C11—C14A	1.495 (7)
O5—C12	1.260 (5)	C11—C14B	1.499 (9)
O6—C12	1.283 (5)	C14A—C15A	1.567 (14)
O7—C13	1.292 (5)	C14A—H14A	0.9700
O7—H6	0.8200	C14A—H14B	0.9700
O8—C13	1.238 (5)	C15A—C16A	1.505 (11)
N1—C3	1.332 (5)	C15A—H15A	0.9700
N1—C2	1.382 (5)	C15A—H15B	0.9700
N2—C3	1.356 (5)	C16A—H16A	0.9600
N2—C1	1.369 (5)	C16A—H16B	0.9600
N2—H2	0.8771	C16A—H16C	0.9600
N3—C11	1.344 (5)	C14B—C15B	1.571 (14)
N3—C9	1.373 (5)	C14B—H14C	0.9700
N4—C11	1.358 (5)	C14B—H14D	0.9700
N4—C10	1.367 (5)	C15B—C16B	1.495 (12)
N4—H4	0.8708	C15B—H15C	0.9700
C1—C2	1.371 (6)	C15B—H15D	0.9700
C1—C5	1.474 (6)	C16B—H16D	0.9600
C2—C4	1.487 (6)	C16B—H16E	0.9600
C3—C6B	1.50 (5)	C16B—H16F	0.9600
C3—C6A	1.510 (12)	O1W—H1W	0.8500
C6A—C7A	1.472 (14)	O1W—H2W	0.8500
C6A—H6A	0.9700	O2W—H3W	0.8501
C6A—H6B	0.9700	O2W—H4W	0.8500
C7A—C8A	1.553 (9)	O3W—H5W	0.8499
C7A—H7A	0.9700	O3W—H6W	0.8551
C7A—H7B	0.9700	O4W—H7W	0.8500
C8A—H8A	0.9600	O4W—H8W	0.8500
C8A—H8B	0.9600	O5W—H9W	0.8500
C8A—H8C	0.9600	O5W—H10W	0.8500
C6B—C7B	1.482 (17)	O6W—H11W	0.8500
C6B—H6C	0.9700	O6W—H12W	0.8500
O1W—Mn1—O2W	89.56 (13)	C8B—C7B—H7C	109.8
O1W—Mn1—O3	93.19 (12)	C6B—C7B—H7D	109.8
O2W—Mn1—O3	94.68 (12)	C8B—C7B—H7D	109.8
O1W—Mn1—N1	167.13 (13)	H7C—C7B—H7D	108.3
O2W—Mn1—N1	86.66 (12)	C7B—C8B—H8D	109.5
O3—Mn1—N1	74.89 (12)	C7B—C8B—H8E	109.5
O1W—Mn1—O5	91.53 (12)	H8D—C8B—H8E	109.5
O2W—Mn1—O5	95.47 (12)	C7B—C8B—H8F	109.5
O3—Mn1—O5	168.84 (11)	H8D—C8B—H8F	109.5
N1—Mn1—O5	101.07 (12)	H8E—C8B—H8F	109.5
O1W—Mn1—N3	89.97 (12)	N3—C9—C10	110.4 (3)
O2W—Mn1—N3	169.81 (13)	N3—C9—C12	118.4 (3)
O3—Mn1—N3	95.51 (11)	C10—C9—C12	131.2 (4)
N1—Mn1—N3	95.91 (12)	N4—C10—C9	105.1 (3)
O5—Mn1—N3	74.37 (11)	N4—C10—C13	122.0 (4)
C5—O1—H1	109.5	C9—C10—C13	132.9 (4)
C4—O3—Mn1	118.1 (3)	N3—C11—N4	109.9 (4)
C12—O5—Mn1	116.7 (3)	N3—C11—C14A	125.3 (13)
C13—O7—H6	109.5	N4—C11—C14A	122.8 (12)
C3—N1—C2	105.4 (3)	N3—C11—C14B	125.4 (15)
C3—N1—Mn1	142.5 (3)	N4—C11—C14B	123.9 (15)
C2—N1—Mn1	112.1 (3)	C14A—C11—C14B	21.4 (9)
C3—N2—C1	108.2 (4)	O5—C12—O6	122.5 (4)
C3—N2—H2	120.0	O5—C12—C9	118.2 (4)
C1—N2—H2	131.8	O6—C12—C9	119.3 (4)
C11—N3—C9	105.7 (3)	O8—C13—O7	123.3 (4)
C11—N3—Mn1	141.8 (3)	O8—C13—C10	120.2 (4)
C9—N3—Mn1	111.8 (3)	O7—C13—C10	116.4 (4)
C11—N4—C10	108.9 (3)	C11—C14A—C15A	111.1 (7)
C11—N4—H4	121.3	C11—C14A—H14A	109.4
C10—N4—H4	129.8	C15A—C14A—H14A	109.4
N2—C1—C2	105.5 (4)	C11—C14A—H14B	109.4
N2—C1—C5	120.8 (4)	C15A—C14A—H14B	109.4
C2—C1—C5	133.7 (4)	H14A—C14A—H14B	108.0
C1—C2—N1	110.1 (4)	C16A—C15A—C14A	107.5 (10)
C1—C2—C4	131.7 (4)	C16A—C15A—H15A	110.2
N1—C2—C4	118.2 (4)	C14A—C15A—H15A	110.2
N1—C3—N2	110.8 (4)	C16A—C15A—H15B	110.2
N1—C3—C6B	131 (2)	C14A—C15A—H15B	110.2
N2—C3—C6B	115 (2)	H15A—C15A—H15B	108.5
N1—C3—C6A	123.2 (7)	C11—C14B—C15B	110.5 (12)
N2—C3—C6A	125.7 (7)	C11—C14B—H14C	109.5
C6B—C3—C6A	23.1 (13)	C15B—C14B—H14C	109.5
O4—C4—O3	125.2 (4)	C11—C14B—H14D	109.5
O4—C4—C2	118.1 (4)	C15B—C14B—H14D	109.5
O3—C4—C2	116.8 (4)	H14C—C14B—H14D	108.1
O2—C5—O1	121.7 (4)	C16B—C15B—C14B	111.5 (16)
O2—C5—C1	121.2 (5)	C16B—C15B—H15C	109.3
O1—C5—C1	117.0 (4)	C14B—C15B—H15C	109.3
C7A—C6A—C3	112.0 (8)	C16B—C15B—H15D	109.3
C7A—C6A—H6A	109.2	C14B—C15B—H15D	109.3
C3—C6A—H6A	109.2	H15C—C15B—H15D	108.0
C7A—C6A—H6B	109.2	C15B—C16B—H16D	109.5
C3—C6A—H6B	109.2	C15B—C16B—H16E	109.5
H6A—C6A—H6B	107.9	H16D—C16B—H16E	109.5
C6A—C7A—C8A	111.0 (8)	C15B—C16B—H16F	109.5
C6A—C7A—H7A	109.4	H16D—C16B—H16F	109.5
C8A—C7A—H7A	109.4	H16E—C16B—H16F	109.5
C6A—C7A—H7B	109.4	Mn1—O1W—H1W	111.4
C8A—C7A—H7B	109.4	Mn1—O1W—H2W	121.1
H7A—C7A—H7B	108.0	H1W—O1W—H2W	118.1
C7B—C6B—C3	109 (3)	Mn1—O2W—H3W	127.0
C7B—C6B—H6C	110.0	Mn1—O2W—H4W	117.6
C3—C6B—H6C	110.0	H3W—O2W—H4W	109.8
C7B—C6B—H6D	110.0	H5W—O3W—H6W	93.8
C3—C6B—H6D	110.0	H7W—O4W—H8W	135.3
H6C—C6B—H6D	108.3	H9W—O5W—H10W	106.9
C6B—C7B—C8B	109 (3)	H11W—O6W—H12W	99.7
C6B—C7B—H7C	109.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.70	2.507 (5)	167.
O7—H6···O6	0.82	1.64	2.462 (4)	175.
N2—H2···O4W	0.88	1.88	2.762 (6)	179.
N4—H4···O6W	0.87	1.90	2.758 (5)	166.
O1W—H1W···O5Wi	0.85	2.25	2.667 (4)	110.
O1W—H2W···O8ii	0.85	1.89	2.724 (4)	168.
O2W—H3W···O8iii	0.85	2.09	2.878 (4)	153.
O2W—H4W···O2iv	0.85	1.97	2.791 (4)	163.
O3W—H5W···O3Wv	0.85	1.48	2.149 (12)	133.
O3W—H5W···O3iv	0.85	2.21	2.811 (6)	128.
O3W—H6W···O3vi	0.86	1.98	2.793 (7)	157.
O4W—H7W···O3W	0.85	1.82	2.646 (7)	165.
O4W—H8W···O7vii	0.85	2.05	2.897 (5)	176.
O5W—H9W···O5vii	0.85	2.09	2.885 (4)	156.
O5W—H9W···O6vii	0.85	2.59	3.266 (5)	137.
O5W—H10W···O4viii	0.85	1.97	2.804 (4)	166.
O6W—H11W···O3Wviii	0.85	1.86	2.674 (7)	160.
O6W—H12W···O5Wix	0.85	2.26	2.880 (6)	130.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.70	2.507 (5)	167
O7—H6⋯O6	0.82	1.64	2.462 (4)	175
N2—H2⋯O4W	0.88	1.88	2.762 (6)	179
N4—H4⋯O6W	0.87	1.90	2.758 (5)	166
O1W—H1W⋯O5Wi	0.85	2.25	2.667 (4)	110
O1W—H2W⋯O8ii	0.85	1.89	2.724 (4)	168
O2W—H3W⋯O8iii	0.85	2.09	2.878 (4)	153
O2W—H4W⋯O2iv	0.85	1.97	2.791 (4)	163
O3W—H5W⋯O3Wv	0.85	1.48	2.149 (12)	133
O3W—H5W⋯O3iv	0.85	2.21	2.811 (6)	128
O3W—H6W⋯O3vi	0.86	1.98	2.793 (7)	157
O4W—H7W⋯O3W	0.85	1.82	2.646 (7)	165
O4W—H8W⋯O7vii	0.85	2.05	2.897 (5)	176
O5W—H9W⋯O5vii	0.85	2.09	2.885 (4)	156
O5W—H9W⋯O6vii	0.85	2.59	3.266 (5)	137
O5W—H10W⋯O4viii	0.85	1.97	2.804 (4)	166
O6W—H11W⋯O3Wviii	0.85	1.86	2.674 (7)	160
O6W—H12W⋯O5Wix	0.85	2.26	2.880 (6)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .