Diacetato[N,N'-bis-(2-pyridylmethyl-idene)cyclo-hexane-1,2-diamine]manganese(II) hexa-hydrate.

The asymmetric unit of the title compound, [Mn(C(2)H(3)O(2))(2)(C(18)H(20)N(4))]·6H(2)O, consists of a neutral Mn(II) complex with six solvent water mol-ecules. In the complex, the Mn(2+) ion is eight-coordinated in a distorted square-anti-prismatic environment by four N atoms from the tetra-dentate ligand N,N'-bis-(2-pyridylmethyl-idene)cyclo-hexane-1,2-diamine (bpic) and four O atoms from two acetate ligands. The compound displays inter-molecular O-H⋯O hydrogen-bond inter-actions to form various kinds of ring structures and cyclic water clusters.

Related literature

For details of some other Mn(bpic) complexes, see: Hwang & Ha (2007 ▶); Lu et al. (2006 ▶); Schoumacker et al. (2003 ▶). For related literature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Mn(C2H3O2)2(C18H20N4)]·6n class="Chemical">H2O

M = 573.50

Triclinic,

a = 8.5124 (5) Å

b = 11.6768 (7) Å

c = 15.1971 (10) Å

α = 79.049 (1)°

β = 85.195 (1)°

γ = 71.484 (1)°

V = 1405.83 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 243 (2) K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.824, T max = 0.900

11880 measured reflections

5710 independent reflections

4641 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.02

5710 reflections

348 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks glonal, I. DOI: 10.1107/S160053680800353X/dn2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800353X/dn2316Isup2.hkl

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

[Mn(C2H3O2)2(C18H20N4)]·6H2O	Z = 2
Mr = 573.50	F(000) = 606
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5124 (5) Å	Cell parameters from 5115 reflections
b = 11.6768 (7) Å	θ = 2.5–26.4°
c = 15.1971 (10) Å	µ = 0.53 mm−1
α = 79.049 (1)°	T = 243 K
β = 85.195 (1)°	Plate, yellow
γ = 71.484 (1)°	0.25 × 0.25 × 0.20 mm
V = 1405.83 (15) Å3

Bruker SMART 1000 CCD diffractometer	5710 independent reflections
Radiation source: fine-focus sealed tube	4641 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.824, Tmax = 0.900	k = −14→11
11880 measured reflections	l = −19→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3
5710 reflections	(Δ/σ)max < 0.001
348 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.20 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
Mn	0.10542 (3)	0.36835 (2)	0.246905 (18)	0.03241 (11)
O1	−0.00485 (18)	0.21992 (14)	0.23912 (11)	0.0489 (4)
O2	−0.17312 (19)	0.40053 (14)	0.18729 (11)	0.0521 (4)
O3	0.30084 (18)	0.22868 (14)	0.34637 (10)	0.0485 (4)
O4	0.33692 (17)	0.40494 (13)	0.29163 (10)	0.0447 (3)
N1	0.2970 (2)	0.26036 (15)	0.14149 (11)	0.0376 (4)
N2	0.1216 (2)	0.49712 (14)	0.11176 (11)	0.0376 (4)
N3	−0.0140 (2)	0.56946 (14)	0.26365 (11)	0.0394 (4)
N4	−0.0488 (2)	0.38102 (15)	0.38548 (11)	0.0395 (4)
C1	0.3813 (3)	0.14166 (18)	0.15517 (15)	0.0430 (5)
H1	0.3627	0.0930	0.2094	0.052*
C2	0.4955 (3)	0.0858 (2)	0.09360 (16)	0.0472 (5)
H2	0.5521	0.0013	0.1059	0.057*
C3	0.5244 (3)	0.1557 (2)	0.01452 (16)	0.0488 (5)
H3	0.6011	0.1200	−0.0284	0.059*
C4	0.4383 (3)	0.2801 (2)	−0.00113 (14)	0.0442 (5)
H4	0.4565	0.3304	−0.0545	0.053*
C5	0.3251 (2)	0.32855 (18)	0.06336 (13)	0.0364 (4)
C6	0.2242 (3)	0.45858 (18)	0.05085 (13)	0.0416 (5)
H6	0.2361	0.5124	−0.0019	0.050*
C7	0.0127 (3)	0.62390 (18)	0.10445 (14)	0.0421 (5)
H7	−0.1019	0.6233	0.0986	0.051*
C8	0.0499 (3)	0.71342 (19)	0.02540 (15)	0.0518 (6)
H8A	0.0345	0.6888	−0.0306	0.062*
H8B	0.1658	0.7111	0.0268	0.062*
C9	−0.0627 (3)	0.8432 (2)	0.02776 (17)	0.0600 (6)
H9A	−0.0326	0.8997	−0.0221	0.072*
H9B	−0.1778	0.8473	0.0205	0.072*
C10	−0.0483 (3)	0.8819 (2)	0.11493 (18)	0.0613 (7)
H10A	−0.1237	0.9650	0.1156	0.074*
H10B	0.0650	0.8831	0.1204	0.074*
C11	−0.0909 (3)	0.79408 (19)	0.19376 (16)	0.0533 (6)
H11A	−0.0782	0.8195	0.2499	0.064*
H11B	−0.2067	0.7973	0.1904	0.064*
C12	0.0206 (3)	0.66403 (18)	0.19347 (14)	0.0448 (5)
H12	0.1359	0.6625	0.2003	0.054*
C13	−0.1067 (3)	0.59486 (19)	0.33081 (14)	0.0476 (5)
H13	−0.1608	0.6770	0.3365	0.057*
C14	−0.1294 (3)	0.49444 (19)	0.40028 (14)	0.0428 (5)
C15	−0.2256 (3)	0.5172 (2)	0.47669 (16)	0.0625 (7)
H15	−0.2823	0.5981	0.4845	0.075*
C16	−0.2375 (3)	0.4208 (2)	0.54085 (16)	0.0628 (7)
H16	−0.3011	0.4344	0.5937	0.075*
C17	−0.1552 (3)	0.3041 (2)	0.52677 (15)	0.0542 (6)
H17	−0.1617	0.2360	0.5696	0.065*
C18	−0.0623 (3)	0.2882 (2)	0.44841 (15)	0.0478 (5)
H18	−0.0059	0.2078	0.4391	0.057*
C19	−0.1417 (3)	0.2873 (2)	0.20639 (13)	0.0395 (5)
C20	−0.2647 (3)	0.2269 (2)	0.18806 (15)	0.0492 (5)
H20A	−0.3731	0.2876	0.1794	0.074*
H20B	−0.2702	0.1633	0.2385	0.074*
H20C	−0.2300	0.1908	0.1344	0.074*
C21	0.3823 (2)	0.30202 (19)	0.34188 (13)	0.0399 (5)
C22	0.5335 (3)	0.2686 (2)	0.39741 (16)	0.0576 (6)
H22A	0.5028	0.2529	0.4604	0.086*
H22B	0.5805	0.3357	0.3863	0.086*
H22C	0.6146	0.1955	0.3813	0.086*
O1W	0.2901 (2)	0.00775 (14)	0.43614 (12)	0.0567 (4)
H1WA	0.3031	0.0826	0.4108	0.070 (8)*
H1WB	0.2780	0.0170	0.4826	0.30 (4)*
O2W	0.1964 (3)	0.0360 (3)	0.61170 (14)	0.0812 (6)
H2WA	0.1671	0.1024	0.6022	0.13 (2)*
H2WB	0.1013	0.0375	0.6368	0.139 (16)*
O3W	0.4248 (2)	0.1469 (2)	0.63610 (18)	0.0914 (7)
H3WA	0.5088	0.1076	0.6083	0.091 (11)*
H3WB	0.4604	0.1624	0.6875	0.18 (2)*
O4W	0.5080 (2)	0.56612 (16)	0.21655 (16)	0.0819 (6)
H4WA	0.6103	0.5220	0.2098	0.085 (10)*
H4WB	0.4635	0.5085	0.2389	0.103 (12)*
O5W	0.4092 (3)	0.81922 (17)	0.22246 (14)	0.0772 (6)
H5WA	0.4297	0.7432	0.2268	0.080 (10)*
H5WB	0.3272	0.8234	0.2554	0.17 (2)*
O6W	0.1096 (2)	−0.02700 (15)	0.30287 (12)	0.0592 (4)
H6WA	0.0627	0.0545	0.2760	0.082 (9)*
H6WB	0.1642	0.0000	0.3400	0.161 (18)*

	U11	U22	U33	U12	U13	U23
Mn	0.03681 (18)	0.02715 (17)	0.03107 (17)	−0.00713 (12)	0.00063 (12)	−0.00511 (11)
O1	0.0391 (8)	0.0549 (9)	0.0551 (9)	−0.0131 (7)	0.0003 (7)	−0.0183 (7)
O2	0.0579 (10)	0.0514 (10)	0.0519 (9)	−0.0249 (8)	0.0013 (7)	−0.0086 (7)
O3	0.0504 (9)	0.0487 (9)	0.0446 (9)	−0.0162 (7)	0.0017 (7)	−0.0035 (7)
O4	0.0431 (8)	0.0404 (8)	0.0479 (9)	−0.0090 (6)	−0.0052 (7)	−0.0058 (7)
N1	0.0417 (9)	0.0353 (9)	0.0366 (9)	−0.0122 (7)	0.0025 (7)	−0.0089 (7)
N2	0.0489 (10)	0.0310 (8)	0.0326 (9)	−0.0115 (7)	0.0006 (7)	−0.0065 (7)
N3	0.0495 (10)	0.0320 (9)	0.0340 (9)	−0.0082 (8)	−0.0002 (8)	−0.0068 (7)
N4	0.0417 (9)	0.0379 (9)	0.0348 (9)	−0.0052 (7)	−0.0004 (7)	−0.0092 (7)
C1	0.0497 (12)	0.0344 (11)	0.0450 (12)	−0.0122 (9)	0.0014 (10)	−0.0098 (9)
C2	0.0443 (12)	0.0395 (12)	0.0587 (14)	−0.0078 (10)	−0.0027 (10)	−0.0185 (10)
C3	0.0407 (12)	0.0544 (14)	0.0553 (14)	−0.0120 (10)	0.0079 (10)	−0.0274 (11)
C4	0.0466 (12)	0.0530 (13)	0.0375 (11)	−0.0198 (10)	0.0077 (9)	−0.0144 (9)
C5	0.0417 (11)	0.0382 (11)	0.0327 (10)	−0.0155 (9)	0.0019 (8)	−0.0104 (8)
C6	0.0556 (13)	0.0395 (11)	0.0316 (10)	−0.0190 (10)	0.0047 (9)	−0.0059 (8)
C7	0.0520 (13)	0.0342 (11)	0.0392 (11)	−0.0123 (9)	−0.0010 (9)	−0.0058 (8)
C8	0.0720 (16)	0.0378 (12)	0.0405 (12)	−0.0146 (11)	0.0032 (11)	−0.0006 (9)
C9	0.0719 (16)	0.0416 (13)	0.0589 (16)	−0.0143 (12)	0.0001 (12)	0.0035 (11)
C10	0.0750 (17)	0.0353 (12)	0.0701 (17)	−0.0155 (12)	0.0096 (13)	−0.0081 (11)
C11	0.0665 (15)	0.0360 (12)	0.0536 (14)	−0.0103 (11)	0.0073 (11)	−0.0120 (10)
C12	0.0553 (13)	0.0353 (11)	0.0421 (12)	−0.0117 (10)	0.0017 (10)	−0.0078 (9)
C13	0.0587 (14)	0.0331 (11)	0.0427 (12)	−0.0014 (10)	0.0058 (10)	−0.0116 (9)
C14	0.0481 (12)	0.0410 (11)	0.0343 (11)	−0.0042 (9)	0.0012 (9)	−0.0118 (9)
C15	0.0778 (18)	0.0511 (14)	0.0487 (14)	−0.0061 (13)	0.0186 (12)	−0.0176 (11)
C16	0.0758 (18)	0.0690 (17)	0.0383 (13)	−0.0157 (14)	0.0151 (12)	−0.0153 (12)
C17	0.0607 (15)	0.0579 (15)	0.0386 (12)	−0.0159 (12)	0.0033 (11)	−0.0013 (10)
C18	0.0547 (13)	0.0380 (11)	0.0436 (12)	−0.0076 (10)	0.0010 (10)	−0.0029 (9)
C19	0.0418 (12)	0.0518 (13)	0.0311 (10)	−0.0206 (10)	0.0081 (9)	−0.0150 (9)
C20	0.0476 (13)	0.0617 (14)	0.0465 (13)	−0.0258 (11)	0.0011 (10)	−0.0144 (11)
C21	0.0362 (11)	0.0473 (12)	0.0329 (10)	−0.0055 (9)	0.0035 (8)	−0.0138 (9)
C22	0.0445 (13)	0.0690 (16)	0.0508 (14)	−0.0004 (12)	−0.0108 (11)	−0.0150 (12)
O1W	0.0722 (11)	0.0445 (9)	0.0502 (10)	−0.0161 (8)	0.0028 (8)	−0.0054 (7)
O2W	0.0723 (14)	0.105 (2)	0.0708 (14)	−0.0352 (12)	0.0181 (11)	−0.0214 (12)
O3W	0.0600 (12)	0.0983 (16)	0.1221 (19)	−0.0099 (11)	0.0115 (12)	−0.0648 (15)
O4W	0.0647 (13)	0.0402 (10)	0.1278 (19)	−0.0123 (9)	0.0159 (11)	0.0025 (10)
O5W	0.0905 (15)	0.0564 (13)	0.0820 (14)	−0.0182 (10)	0.0101 (12)	−0.0188 (10)
O6W	0.0592 (10)	0.0523 (10)	0.0660 (11)	−0.0178 (8)	0.0009 (9)	−0.0097 (8)

Mn—O1	2.2425 (15)	C9—H9B	0.9800
Mn—N3	2.2979 (16)	C10—C11	1.521 (3)
Mn—O4	2.3232 (14)	C10—H10A	0.9800
Mn—N2	2.3257 (16)	C10—H10B	0.9800
Mn—O3	2.3395 (14)	C11—C12	1.514 (3)
Mn—N4	2.3899 (17)	C11—H11A	0.9800
Mn—N1	2.4166 (16)	C11—H11B	0.9800
Mn—O2	2.4997 (15)	C12—H12	0.9900
O1—C19	1.261 (2)	C13—C14	1.472 (3)
O2—C19	1.244 (3)	C13—H13	0.9400
O3—C21	1.251 (3)	C14—C15	1.382 (3)
O4—C21	1.258 (2)	C15—C16	1.366 (3)
N1—C1	1.328 (3)	C15—H15	0.9400
N1—C5	1.347 (2)	C16—C17	1.369 (3)
N2—C6	1.263 (3)	C16—H16	0.9400
N2—C7	1.465 (2)	C17—C18	1.382 (3)
N3—C13	1.258 (3)	C17—H17	0.9400
N3—C12	1.466 (3)	C18—H18	0.9400
N4—C18	1.330 (3)	C19—C20	1.504 (3)
N4—C14	1.336 (3)	C20—H20A	0.9700
C1—C2	1.387 (3)	C20—H20B	0.9700
C1—H1	0.9400	C20—H20C	0.9700
C2—C3	1.370 (3)	C21—C22	1.503 (3)
C2—H2	0.9400	C22—H22A	0.9700
C3—C4	1.388 (3)	C22—H22B	0.9700
C3—H3	0.9400	C22—H22C	0.9700
C4—C5	1.384 (3)	O1W—H1WA	0.922
C4—H4	0.9400	O1W—H1WB	0.728
C5—C6	1.473 (3)	O2W—H2WA	0.724
C6—H6	0.9400	O2W—H2WB	0.862
C7—C8	1.518 (3)	O3W—H3WA	0.846
C7—C12	1.526 (3)	O3W—H3WB	0.929
C7—H7	0.9900	O4W—H4WA	0.868
C8—C9	1.520 (3)	O4W—H4WB	0.875
C8—H8A	0.9800	O5W—H5WA	0.839
C8—H8B	0.9800	O5W—H5WB	0.818
C9—C10	1.505 (4)	O6W—H6WA	0.933
C9—H9A	0.9800	O6W—H6WB	0.916
O1—Mn—N3	131.76 (6)	C9—C8—H8A	109.4
O1—Mn—O4	143.52 (5)	C7—C8—H8B	109.4
N3—Mn—O4	81.25 (6)	C9—C8—H8B	109.4
O1—Mn—N2	115.12 (6)	H8A—C8—H8B	108.0
N3—Mn—N2	70.09 (6)	C10—C9—C8	110.9 (2)
O4—Mn—N2	88.15 (6)	C10—C9—H9A	109.5
O1—Mn—O3	89.34 (5)	C8—C9—H9A	109.5
N3—Mn—O3	122.24 (6)	C10—C9—H9B	109.5
O4—Mn—O3	55.61 (5)	C8—C9—H9B	109.5
N2—Mn—O3	134.37 (6)	H9A—C9—H9B	108.1
O1—Mn—N4	84.05 (6)	C9—C10—C11	110.6 (2)
N3—Mn—N4	69.42 (6)	C9—C10—H10A	109.5
O4—Mn—N4	97.39 (6)	C11—C10—H10A	109.5
N2—Mn—N4	137.68 (6)	C9—C10—H10B	109.5
O3—Mn—N4	79.35 (5)	C11—C10—H10B	109.5
O1—Mn—N1	79.49 (5)	H10A—C10—H10B	108.1
N3—Mn—N1	136.20 (6)	C12—C11—C10	110.97 (19)
O4—Mn—N1	84.34 (5)	C12—C11—H11A	109.4
N2—Mn—N1	68.30 (6)	C10—C11—H11A	109.4
O3—Mn—N1	80.28 (5)	C12—C11—H11B	109.4
N4—Mn—N1	153.85 (6)	C10—C11—H11B	109.4
O1—Mn—O2	54.45 (5)	H11A—C11—H11B	108.0
N3—Mn—O2	81.85 (6)	N3—C12—C11	116.19 (18)
O4—Mn—O2	162.02 (5)	N3—C12—C7	106.13 (16)
N2—Mn—O2	80.34 (5)	C11—C12—C7	111.00 (17)
O3—Mn—O2	140.89 (5)	N3—C12—H12	107.7
N4—Mn—O2	82.32 (5)	C11—C12—H12	107.7
N1—Mn—O2	103.87 (5)	C7—C12—H12	107.7
C19—O1—Mn	97.99 (12)	N3—C13—C14	119.20 (18)
C19—O2—Mn	86.39 (12)	N3—C13—H13	120.4
C21—O3—Mn	91.80 (12)	C14—C13—H13	120.4
C21—O4—Mn	92.38 (12)	N4—C14—C15	122.6 (2)
C1—N1—C5	117.49 (17)	N4—C14—C13	115.85 (18)
C1—N1—Mn	125.96 (14)	C15—C14—C13	121.57 (19)
C5—N1—Mn	116.50 (12)	C16—C15—C14	119.3 (2)
C6—N2—C7	123.33 (17)	C16—C15—H15	120.3
C6—N2—Mn	120.53 (13)	C14—C15—H15	120.3
C7—N2—Mn	116.07 (12)	C15—C16—C17	118.8 (2)
C13—N3—C12	122.54 (17)	C15—C16—H16	120.6
C13—N3—Mn	119.87 (14)	C17—C16—H16	120.6
C12—N3—Mn	117.58 (12)	C16—C17—C18	118.8 (2)
C18—N4—C14	117.34 (18)	C16—C17—H17	120.6
C18—N4—Mn	127.12 (14)	C18—C17—H17	120.6
C14—N4—Mn	115.54 (13)	N4—C18—C17	123.2 (2)
N1—C1—C2	123.4 (2)	N4—C18—H18	118.4
N1—C1—H1	118.3	C17—C18—H18	118.4
C2—C1—H1	118.3	O2—C19—O1	121.13 (19)
C3—C2—C1	118.9 (2)	O2—C19—C20	120.55 (19)
C3—C2—H2	120.5	O1—C19—C20	118.29 (19)
C1—C2—H2	120.5	C19—C20—H20A	109.5
C2—C3—C4	118.8 (2)	C19—C20—H20B	109.5
C2—C3—H3	120.6	H20A—C20—H20B	109.5
C4—C3—H3	120.6	C19—C20—H20C	109.5
C5—C4—C3	118.7 (2)	H20A—C20—H20C	109.5
C5—C4—H4	120.6	H20B—C20—H20C	109.5
C3—C4—H4	120.6	O3—C21—O4	120.18 (18)
N1—C5—C4	122.72 (18)	O3—C21—C22	120.3 (2)
N1—C5—C6	114.99 (17)	O4—C21—C22	119.5 (2)
C4—C5—C6	122.28 (18)	C21—C22—H22A	109.5
N2—C6—C5	119.34 (18)	C21—C22—H22B	109.5
N2—C6—H6	120.3	H22A—C22—H22B	109.5
C5—C6—H6	120.3	C21—C22—H22C	109.5
N2—C7—C8	115.54 (18)	H22A—C22—H22C	109.5
N2—C7—C12	106.62 (15)	H22B—C22—H22C	109.5
C8—C7—C12	111.62 (17)	H1WA—O1W—H1WB	98
N2—C7—H7	107.6	H2WA—O2W—H2WB	88
C8—C7—H7	107.6	H3WA—O3W—H3WB	108
C12—C7—H7	107.6	H4WA—O4W—H4WB	100
C7—C8—C9	111.09 (19)	H5WA—O5W—H5WB	91
C7—C8—H8A	109.4	H6WA—O6W—H6WB	88
N3—Mn—O1—C19	28.31 (15)	N3—Mn—N4—C18	−177.26 (18)
O4—Mn—O1—C19	178.17 (11)	O4—Mn—N4—C18	−99.54 (17)
N2—Mn—O1—C19	−56.78 (13)	N2—Mn—N4—C18	165.06 (16)
O3—Mn—O1—C19	163.13 (12)	O3—Mn—N4—C18	−46.69 (17)
N4—Mn—O1—C19	83.77 (12)	N1—Mn—N4—C18	−7.3 (2)
N1—Mn—O1—C19	−116.63 (13)	O2—Mn—N4—C18	98.60 (17)
O2—Mn—O1—C19	−1.03 (11)	O1—Mn—N4—C14	−136.26 (15)
O1—Mn—O2—C19	1.03 (11)	N3—Mn—N4—C14	2.72 (14)
N3—Mn—O2—C19	−157.30 (13)	O4—Mn—N4—C14	80.45 (15)
O4—Mn—O2—C19	−177.43 (15)	N2—Mn—N4—C14	−14.95 (19)
N2—Mn—O2—C19	131.64 (13)	O3—Mn—N4—C14	133.30 (15)
O3—Mn—O2—C19	−24.61 (16)	N1—Mn—N4—C14	172.66 (14)
N4—Mn—O2—C19	−87.12 (12)	O2—Mn—N4—C14	−81.41 (15)
N1—Mn—O2—C19	67.00 (12)	C5—N1—C1—C2	0.1 (3)
O1—Mn—O3—C21	170.16 (12)	Mn—N1—C1—C2	−176.94 (15)
N3—Mn—O3—C21	−48.56 (14)	N1—C1—C2—C3	0.3 (3)
O4—Mn—O3—C21	0.94 (11)	C1—C2—C3—C4	0.0 (3)
N2—Mn—O3—C21	44.52 (15)	C2—C3—C4—C5	−0.7 (3)
N4—Mn—O3—C21	−105.77 (12)	C1—N1—C5—C4	−0.9 (3)
N1—Mn—O3—C21	90.71 (12)	Mn—N1—C5—C4	176.47 (15)
O2—Mn—O3—C21	−169.22 (11)	C1—N1—C5—C6	178.17 (18)
O1—Mn—O4—C21	−19.26 (17)	Mn—N1—C5—C6	−4.5 (2)
N3—Mn—O4—C21	138.47 (13)	C3—C4—C5—N1	1.2 (3)
N2—Mn—O4—C21	−151.39 (12)	C3—C4—C5—C6	−177.80 (19)
O3—Mn—O4—C21	−0.93 (11)	C7—N2—C6—C5	−178.27 (18)
N4—Mn—O4—C21	70.72 (12)	Mn—N2—C6—C5	4.6 (3)
N1—Mn—O4—C21	−83.02 (12)	N1—C5—C6—N2	0.1 (3)
O2—Mn—O4—C21	158.63 (16)	C4—C5—C6—N2	179.21 (19)
O1—Mn—N1—C1	−55.50 (16)	C6—N2—C7—C8	−10.0 (3)
N3—Mn—N1—C1	162.74 (15)	Mn—N2—C7—C8	167.23 (15)
O4—Mn—N1—C1	91.65 (16)	C6—N2—C7—C12	−134.7 (2)
N2—Mn—N1—C1	−178.08 (18)	Mn—N2—C7—C12	42.56 (19)
O3—Mn—N1—C1	35.63 (16)	N2—C7—C8—C9	−176.28 (19)
N4—Mn—N1—C1	−3.6 (2)	C12—C7—C8—C9	−54.2 (3)
O2—Mn—N1—C1	−104.60 (16)	C7—C8—C9—C10	56.3 (3)
O1—Mn—N1—C5	127.40 (14)	C8—C9—C10—C11	−57.9 (3)
N3—Mn—N1—C5	−14.36 (17)	C9—C10—C11—C12	57.8 (3)
O4—Mn—N1—C5	−85.44 (13)	C13—N3—C12—C11	−13.9 (3)
N2—Mn—N1—C5	4.82 (13)	Mn—N3—C12—C11	165.37 (15)
O3—Mn—N1—C5	−141.47 (14)	C13—N3—C12—C7	−137.8 (2)
N4—Mn—N1—C5	179.31 (13)	Mn—N3—C12—C7	41.4 (2)
O2—Mn—N1—C5	78.31 (14)	C10—C11—C12—N3	−176.85 (19)
O1—Mn—N2—C6	−71.18 (17)	C10—C11—C12—C7	−55.5 (3)
N3—Mn—N2—C6	161.05 (17)	N2—C7—C12—N3	−51.9 (2)
O4—Mn—N2—C6	79.68 (16)	C8—C7—C12—N3	−178.90 (18)
O3—Mn—N2—C6	44.99 (19)	N2—C7—C12—C11	−178.96 (17)
N4—Mn—N2—C6	178.64 (14)	C8—C7—C12—C11	54.0 (2)
N1—Mn—N2—C6	−4.96 (15)	C12—N3—C13—C14	−177.34 (18)
O2—Mn—N2—C6	−114.19 (16)	Mn—N3—C13—C14	3.4 (3)
O1—Mn—N2—C7	111.51 (14)	C18—N4—C14—C15	−0.8 (3)
N3—Mn—N2—C7	−16.27 (13)	Mn—N4—C14—C15	179.20 (18)
O4—Mn—N2—C7	−97.64 (14)	C18—N4—C14—C13	177.84 (19)
O3—Mn—N2—C7	−132.33 (13)	Mn—N4—C14—C13	−2.1 (2)
N4—Mn—N2—C7	1.33 (18)	N3—C13—C14—N4	−0.7 (3)
N1—Mn—N2—C7	177.72 (15)	N3—C13—C14—C15	177.9 (2)
O2—Mn—N2—C7	68.49 (14)	N4—C14—C15—C16	1.1 (4)
O1—Mn—N3—C13	57.80 (19)	C13—C14—C15—C16	−177.4 (2)
O4—Mn—N3—C13	−104.62 (17)	C14—C15—C16—C17	−0.9 (4)
N2—Mn—N3—C13	164.18 (18)	C15—C16—C17—C18	0.4 (4)
O3—Mn—N3—C13	−65.21 (19)	C14—N4—C18—C17	0.3 (3)
N4—Mn—N3—C13	−3.27 (16)	Mn—N4—C18—C17	−179.74 (17)
N1—Mn—N3—C13	−176.88 (15)	C16—C17—C18—N4	−0.1 (4)
O2—Mn—N3—C13	81.55 (17)	Mn—O2—C19—O1	−1.75 (19)
O1—Mn—N3—C12	−121.46 (14)	Mn—O2—C19—C20	−179.73 (18)
O4—Mn—N3—C12	76.12 (14)	Mn—O1—C19—O2	2.0 (2)
N2—Mn—N3—C12	−15.08 (14)	Mn—O1—C19—C20	179.99 (15)
O3—Mn—N3—C12	115.53 (14)	Mn—O3—C21—O4	−1.7 (2)
N4—Mn—N3—C12	177.47 (15)	Mn—O3—C21—C22	177.48 (17)
N1—Mn—N3—C12	3.86 (18)	Mn—O4—C21—O3	1.7 (2)
O2—Mn—N3—C12	−97.71 (14)	Mn—O4—C21—C22	−177.47 (17)
O1—Mn—N4—C18	43.76 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.922	1.793	2.705 (2)	169
O1W—H1WB···O2W	0.728	2.054	2.770 (3)	168
O2W—H2WA···O3W	0.724	2.523	2.738 (3)	100
O2W—H2WB···O6Wi	0.862	1.975	2.835 (3)	176
O3W—H3WA···O1Wii	0.846	1.972	2.807 (3)	169
O3W—H3WB···O5Wiii	0.929	1.915	2.821 (3)	165
O4W—H4WA···O2iv	0.868	1.986	2.845 (2)	170
O4W—H4WB···O4	0.875	1.892	2.759 (2)	171
O5W—H5WA···O4W	0.839	1.993	2.821 (3)	169
O5W—H5WB···O6Wv	0.818	2.281	2.937 (3)	138
O6W—H6WA···O1	0.933	1.820	2.741 (2)	169
O6W—H6WB···O1W	0.916	1.915	2.803 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3	0.922	1.793	2.705 (2)	169
O1W—H1WB⋯O2W	0.728	2.054	2.770 (3)	168
O2W—H2WA⋯O3W	0.724	2.523	2.738 (3)	100
O2W—H2WB⋯O6Wi	0.862	1.975	2.835 (3)	176
O3W—H3WA⋯O1Wii	0.846	1.972	2.807 (3)	169
O3W—H3WB⋯O5Wiii	0.929	1.915	2.821 (3)	165
O4W—H4WA⋯O2iv	0.868	1.986	2.845 (2)	170
O4W—H4WB⋯O4	0.875	1.892	2.759 (2)	171
O5W—H5WA⋯O4W	0.839	1.993	2.821 (3)	169
O5W—H5WB⋯O6Wv	0.818	2.281	2.937 (3)	138
O6W—H6WA⋯O1	0.933	1.820	2.741 (2)	169
O6W—H6WB⋯O1W	0.916	1.915	2.803 (3)	163

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