Oxalatobis(propane-1,3-diamine)manganese(II) chloride monohydrate.

In the asymmetric unit of the title compound, [Mn(C(2)O(4))(C(3)H(10)N(2))(2)]Cl·H(2)O, there are two independent Mn(III) complexes, two Cl(-) anions and two uncoordinated water mol-ecules. Each Mn(III) atom is hexa-coordinated by four N atoms from two propane-1,3-diamine ligands and two O atoms from one oxalate ligand, resulting in a slightly distorted octa-hedral MnO(2)N(4) geometry. Mn-O and Mn-N bond lengths are in the ranges 1.969 (2)-2.020 (3) and 2.068 (3)-2.113 (4) Å, respectively. There are weak inter-molecular O-H⋯O, O-H⋯Cl, N-H⋯O and N-H⋯Cl hydrogen bonds with D⋯A distances in the range 2.831 (4)-3.423 (3) Å.

Related literature

For related literature, see: Chung et al. (1971 ▶); Church & Halvorson (1959 ▶); Okabe & Oya (2000 ▶); Pocker & Fong (1980 ▶); Poowell (1953 ▶); Scapin et al. (1997 ▶); Serre et al. (2005 ▶).

Experimental

Crystal data

[Mn(C2O4)(C3H10N2)2]Cl·H2O

M = 344.69

Monoclinic,

a = 9.1286 (17) Å

b = 11.807 (2) Å

c = 13.912 (3) Å

β = 100.037 (14)°

V = 1476.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.10 mm−1

T = 293 (2) K

0.43 × 0.28 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2001 ▶) T min = 0.650, T max = 0.787

3373 measured reflections

3060 independent reflections

3032 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.00

3060 reflections

356 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.43 e Å−3

Absolute structure: Flack (1983 ▶), 521 Friedel pairs

Flack parameter: 0.040 (15)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065361/is2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065361/is2256Isup2.hkl

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

[Mn(C2O4)(C3H10N2)2]Cl·H2O	F000 = 720
Mr = 344.69	Dx = 1.551 Mg m−3
Monoclinic, Pn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 3060 reflections
a = 9.1286 (17) Å	θ = 2.9–25.0º
b = 11.807 (2) Å	µ = 1.10 mm−1
c = 13.912 (3) Å	T = 293 (2) K
β = 100.037 (14)º	Block, yellow
V = 1476.6 (5) Å3	0.43 × 0.28 × 0.23 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3060 independent reflections
Radiation source: fine-focus sealed tube	3032 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −1→10
Tmin = 0.650, Tmax = 0.787	k = −14→1
3373 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.072P)2 + 0.2126P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.53 e Å−3
3060 reflections	Δρmin = −0.43 e Å−3
356 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
8 restraints	Extinction coefficient: 0.0164 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 521 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.040 (15)

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
Mn1	0.11279 (5)	0.45504 (4)	0.50737 (3)	0.02681 (15)
Mn2	0.91703 (6)	0.99201 (4)	0.36505 (4)	0.02996 (16)
C1	0.3604 (4)	0.3805 (3)	0.3916 (3)	0.0360 (8)
H1A	0.3263	0.4355	0.3409	0.043*
H1B	0.4034	0.3172	0.3619	0.043*
C2	0.4805 (5)	0.4350 (4)	0.4694 (3)	0.0404 (9)
H2A	0.5053	0.3832	0.5239	0.048*
H2B	0.5697	0.4471	0.4417	0.048*
C3	0.4322 (5)	0.5455 (3)	0.5062 (3)	0.0378 (9)
H3A	0.3975	0.5942	0.4508	0.045*
H3B	0.5178	0.5818	0.5453	0.045*
C4	−0.1361 (5)	0.5164 (3)	0.6257 (3)	0.0373 (8)
H4A	−0.2080	0.4832	0.5738	0.045*
H4B	−0.1848	0.5778	0.6541	0.045*
C5	−0.0860 (5)	0.4271 (3)	0.7035 (3)	0.0401 (9)
H5A	−0.0135	0.4604	0.7550	0.048*
H5B	−0.1709	0.4035	0.7319	0.048*
C6	−0.0192 (5)	0.3260 (3)	0.6642 (3)	0.0351 (8)
H6A	−0.0886	0.2967	0.6090	0.042*
H6B	−0.0038	0.2677	0.7140	0.042*
C7	−0.1264 (4)	0.4394 (3)	0.3465 (3)	0.0289 (7)
C8	−0.0207 (4)	0.5353 (3)	0.3226 (3)	0.0308 (8)
C9	0.5848 (5)	0.9640 (4)	0.3832 (3)	0.0417 (9)
H9A	0.4953	0.9199	0.3620	0.050*
H9B	0.6156	0.9518	0.4527	0.050*
C10	0.5504 (5)	1.0872 (4)	0.3649 (4)	0.0486 (10)
H10A	0.4667	1.1079	0.3957	0.058*
H10B	0.5214	1.0994	0.2952	0.058*
C11	0.6810 (5)	1.1632 (3)	0.4035 (3)	0.0431 (9)
H11A	0.6490	1.2416	0.3972	0.052*
H11B	0.7139	1.1477	0.4723	0.052*
C12	1.0022 (5)	1.0344 (3)	0.5651 (3)	0.0377 (9)
C13	1.1333 (5)	1.0806 (3)	0.5152 (3)	0.0360 (8)
C14	1.1008 (6)	0.9676 (4)	0.1977 (3)	0.0478 (11)
H14A	1.1031	0.9793	0.1290	0.057*
H14B	1.1750	1.0167	0.2349	0.057*
C15	1.1384 (6)	0.8483 (4)	0.2233 (4)	0.0516 (11)
H15A	1.2274	0.8282	0.1979	0.062*
H15B	1.0582	0.8004	0.1913	0.062*
C16	1.1650 (5)	0.8233 (4)	0.3342 (3)	0.0428 (9)
H16A	1.2009	0.7463	0.3452	0.051*
H16B	1.2415	0.8738	0.3670	0.051*
N1	1.0262 (4)	0.8377 (2)	0.3781 (2)	0.0324 (6)
H1C	1.0502	0.8218	0.4422	0.039*
H1D	0.9606	0.7847	0.3515	0.039*
N2	0.9487 (5)	0.9993 (3)	0.2183 (2)	0.0375 (8)
H2C	0.8814	0.9534	0.1829	0.045*
H2D	0.9284	1.0704	0.1965	0.045*
N3	0.7056 (4)	0.9230 (2)	0.3304 (2)	0.0327 (7)
H3C	0.6738	0.9341	0.2662	0.039*
H3D	0.7143	0.8477	0.3398	0.039*
N4	0.8095 (4)	1.1468 (3)	0.3503 (2)	0.0340 (7)
H4C	0.8773	1.2009	0.3706	0.041*
H4D	0.7762	1.1586	0.2863	0.041*
N5	0.3116 (4)	0.5354 (2)	0.5663 (2)	0.0291 (6)
H5C	0.2889	0.6059	0.5835	0.035*
H5D	0.3501	0.4987	0.6217	0.035*
N6	0.2302 (4)	0.3396 (2)	0.4346 (2)	0.0297 (6)
H6C	0.2630	0.2837	0.4769	0.036*
H6D	0.1648	0.3083	0.3860	0.036*
N7	0.1268 (4)	0.3507 (2)	0.6321 (2)	0.0313 (6)
H7A	0.1688	0.2845	0.6197	0.038*
H7B	0.1877	0.3841	0.6818	0.038*
N8	−0.0078 (4)	0.5630 (2)	0.5835 (2)	0.0319 (6)
H8A	0.0568	0.5937	0.6330	0.038*
H8B	−0.0430	0.6199	0.5430	0.038*
O1	0.0942 (3)	0.55365 (19)	0.39175 (18)	0.0302 (5)
O2	−0.0783 (3)	0.3917 (2)	0.43141 (18)	0.0301 (5)
O3	−0.2391 (3)	0.4152 (2)	0.2880 (2)	0.0402 (6)
O4	−0.0474 (4)	0.5855 (3)	0.24339 (19)	0.0440 (7)
O5	1.0023 (5)	1.0508 (3)	0.6534 (2)	0.0583 (9)
O6	0.8993 (3)	0.9836 (2)	0.50604 (19)	0.0362 (6)
O7	1.1132 (3)	1.0658 (2)	0.42064 (19)	0.0365 (6)
O8	1.2408 (4)	1.1305 (2)	0.5639 (2)	0.0457 (7)
O9	0.0571 (4)	0.2740 (3)	0.2343 (2)	0.0600 (9)
H1W	0.114 (5)	0.246 (5)	0.201 (4)	0.072*
H2W	−0.031 (2)	0.256 (6)	0.214 (4)	0.072*
O10	0.7709 (7)	0.7953 (3)	0.6200 (3)	0.0795 (13)
H3W	0.828 (7)	0.772 (6)	0.586 (4)	0.095*
H4W	0.728 (8)	0.854 (4)	0.603 (5)	0.095*
Cl1	0.72741 (14)	0.19856 (8)	0.10470 (7)	0.0495 (3)
Cl2	0.72971 (12)	0.67594 (8)	0.41008 (8)	0.0427 (2)

	U11	U22	U33	U12	U13	U23
Mn1	0.0300 (3)	0.0243 (2)	0.0252 (2)	−0.0010 (2)	0.00198 (19)	0.00041 (19)
Mn2	0.0339 (3)	0.0262 (3)	0.0277 (3)	−0.0024 (2)	−0.0005 (2)	0.00098 (18)
C1	0.0375 (19)	0.0338 (18)	0.0389 (18)	−0.0004 (16)	0.0132 (17)	−0.0015 (14)
C2	0.034 (2)	0.0431 (19)	0.044 (2)	0.0002 (18)	0.0074 (18)	0.0010 (17)
C3	0.038 (2)	0.036 (2)	0.039 (2)	−0.0106 (16)	0.0072 (17)	−0.0029 (15)
C4	0.039 (2)	0.0368 (18)	0.0375 (19)	0.0047 (16)	0.0108 (17)	−0.0016 (15)
C5	0.044 (2)	0.040 (2)	0.038 (2)	0.0020 (19)	0.0125 (18)	0.0046 (16)
C6	0.042 (2)	0.0303 (17)	0.0341 (18)	−0.0043 (16)	0.0088 (17)	0.0045 (14)
C7	0.0311 (19)	0.0277 (15)	0.0270 (16)	−0.0012 (14)	0.0025 (15)	−0.0032 (12)
C8	0.037 (2)	0.0277 (17)	0.0276 (17)	0.0020 (15)	0.0042 (16)	0.0006 (13)
C9	0.037 (2)	0.044 (2)	0.045 (2)	−0.0050 (18)	0.0078 (18)	0.0003 (17)
C10	0.037 (2)	0.045 (2)	0.062 (3)	0.0071 (19)	0.005 (2)	−0.002 (2)
C11	0.049 (2)	0.0307 (18)	0.051 (2)	0.0075 (18)	0.0103 (19)	−0.0051 (16)
C12	0.048 (2)	0.0302 (17)	0.032 (2)	0.0042 (17)	−0.0012 (18)	0.0017 (14)
C13	0.036 (2)	0.0230 (15)	0.043 (2)	0.0026 (16)	−0.0082 (17)	0.0000 (15)
C14	0.061 (3)	0.044 (2)	0.044 (2)	0.001 (2)	0.022 (2)	0.0083 (18)
C15	0.068 (3)	0.040 (2)	0.052 (2)	0.013 (2)	0.025 (2)	0.0015 (19)
C16	0.039 (2)	0.0382 (19)	0.052 (2)	0.0076 (17)	0.0103 (18)	0.0076 (17)
N1	0.0350 (15)	0.0268 (13)	0.0335 (15)	−0.0003 (13)	0.0005 (13)	0.0046 (12)
N2	0.052 (2)	0.0294 (16)	0.0305 (16)	0.0041 (14)	0.0041 (15)	0.0026 (11)
N3	0.0333 (16)	0.0261 (14)	0.0348 (15)	−0.0006 (13)	−0.0049 (13)	0.0040 (12)
N4	0.0404 (17)	0.0233 (13)	0.0361 (16)	−0.0014 (13)	0.0003 (14)	0.0002 (11)
N5	0.0293 (16)	0.0256 (14)	0.0298 (15)	−0.0026 (12)	−0.0021 (13)	−0.0019 (11)
N6	0.0374 (16)	0.0235 (12)	0.0284 (14)	−0.0014 (13)	0.0063 (12)	0.0001 (11)
N7	0.0385 (16)	0.0265 (13)	0.0276 (14)	−0.0007 (13)	0.0023 (13)	0.0000 (11)
N8	0.0369 (17)	0.0257 (12)	0.0322 (15)	0.0019 (13)	0.0033 (14)	−0.0001 (11)
O1	0.0371 (14)	0.0263 (11)	0.0244 (11)	−0.0045 (10)	−0.0022 (10)	0.0027 (9)
O2	0.0336 (12)	0.0258 (10)	0.0291 (11)	−0.0037 (10)	0.0003 (10)	−0.0006 (9)
O3	0.0378 (16)	0.0410 (14)	0.0380 (13)	−0.0050 (13)	−0.0041 (13)	−0.0037 (12)
O4	0.0555 (18)	0.0412 (14)	0.0300 (13)	−0.0042 (14)	−0.0072 (13)	0.0097 (11)
O5	0.073 (2)	0.069 (2)	0.0287 (15)	−0.0011 (19)	−0.0039 (16)	−0.0109 (13)
O6	0.0444 (17)	0.0346 (12)	0.0281 (13)	−0.0032 (12)	0.0018 (12)	0.0045 (10)
O7	0.0375 (15)	0.0334 (13)	0.0356 (14)	−0.0069 (12)	−0.0019 (12)	0.0007 (11)
O8	0.0472 (17)	0.0290 (13)	0.0522 (16)	−0.0039 (12)	−0.0155 (14)	−0.0002 (12)
O9	0.059 (2)	0.074 (2)	0.0471 (17)	0.0031 (19)	0.0081 (16)	−0.0112 (16)
O10	0.122 (4)	0.048 (2)	0.081 (3)	−0.007 (2)	0.052 (3)	−0.0004 (19)
Cl1	0.0658 (7)	0.0332 (4)	0.0420 (5)	−0.0013 (5)	−0.0118 (5)	0.0025 (4)
Cl2	0.0448 (5)	0.0307 (4)	0.0529 (5)	0.0008 (4)	0.0090 (4)	0.0068 (4)

Mn1—O1	1.969 (2)	C10—C11	1.514 (7)
Mn1—O2	2.019 (3)	C10—H10A	0.9700
Mn1—N5	2.085 (3)	C10—H10B	0.9700
Mn1—N8	2.089 (3)	C11—N4	1.504 (5)
Mn1—N6	2.100 (3)	C11—H11A	0.9700
Mn1—N7	2.113 (3)	C11—H11B	0.9700
Mn2—O6	1.999 (3)	C12—O5	1.243 (5)
Mn2—O7	2.020 (3)	C12—O6	1.284 (5)
Mn2—N4	2.068 (3)	C12—C13	1.582 (6)
Mn2—N1	2.069 (3)	C13—O8	1.241 (5)
Mn2—N3	2.073 (3)	C13—O7	1.307 (5)
Mn2—N2	2.113 (4)	C14—C15	1.478 (6)
C1—N6	1.500 (5)	C14—N2	1.513 (7)
C1—C2	1.541 (6)	C14—H14A	0.9700
C1—H1A	0.9700	C14—H14B	0.9700
C1—H1B	0.9700	C15—C16	1.548 (6)
C2—C3	1.495 (6)	C15—H15A	0.9700
C2—H2A	0.9700	C15—H15B	0.9700
C2—H2B	0.9700	C16—N1	1.509 (5)
C3—N5	1.499 (5)	C16—H16A	0.9700
C3—H3A	0.9700	C16—H16B	0.9700
C3—H3B	0.9700	N1—H1C	0.9000
C4—N8	1.503 (5)	N1—H1D	0.9000
C4—C5	1.523 (6)	N2—H2C	0.9000
C4—H4A	0.9700	N2—H2D	0.9000
C4—H4B	0.9700	N3—H3C	0.9000
C5—C6	1.488 (6)	N3—H3D	0.9000
C5—H5A	0.9700	N4—H4C	0.9000
C5—H5B	0.9700	N4—H4D	0.9000
C6—N7	1.506 (5)	N5—H5C	0.9000
C6—H6A	0.9700	N5—H5D	0.9000
C6—H6B	0.9700	N6—H6C	0.9000
C7—O3	1.229 (5)	N6—H6D	0.9000
C7—O2	1.314 (4)	N7—H7A	0.9000
C7—C8	1.560 (5)	N7—H7B	0.9000
C8—O4	1.238 (5)	N8—H8A	0.9000
C8—O1	1.311 (5)	N8—H8B	0.9000
C9—C10	1.501 (6)	O9—H1W	0.82 (5)
C9—N3	1.507 (6)	O9—H2W	0.83 (3)
C9—H9A	0.9700	O10—H3W	0.81 (6)
C9—H9B	0.9700	O10—H4W	0.81 (5)
O1—Mn1—O2	81.23 (11)	N4—C11—C10	112.5 (3)
O1—Mn1—N5	89.86 (12)	N4—C11—H11A	109.1
O2—Mn1—N5	171.03 (11)	C10—C11—H11A	109.1
O1—Mn1—N8	94.33 (11)	N4—C11—H11B	109.1
O2—Mn1—N8	90.45 (12)	C10—C11—H11B	109.1
N5—Mn1—N8	91.28 (13)	H11A—C11—H11B	107.8
O1—Mn1—N6	88.21 (11)	O5—C12—O6	125.4 (4)
O2—Mn1—N6	88.53 (11)	O5—C12—C13	120.6 (4)
N5—Mn1—N6	90.15 (12)	O6—C12—C13	113.9 (3)
N8—Mn1—N6	177.09 (12)	O8—C13—O7	124.9 (4)
O1—Mn1—N7	178.39 (13)	O8—C13—C12	120.7 (4)
O2—Mn1—N7	97.88 (11)	O7—C13—C12	114.3 (3)
N5—Mn1—N7	91.05 (12)	C15—C14—N2	111.9 (4)
N8—Mn1—N7	84.33 (12)	C15—C14—H14A	109.2
N6—Mn1—N7	93.11 (12)	N2—C14—H14A	109.2
O6—Mn2—O7	82.17 (12)	C15—C14—H14B	109.2
O6—Mn2—N4	91.31 (12)	N2—C14—H14B	109.2
O7—Mn2—N4	91.72 (12)	H14A—C14—H14B	107.9
O6—Mn2—N1	89.44 (12)	C14—C15—C16	114.3 (4)
O7—Mn2—N1	88.01 (12)	C14—C15—H15A	108.7
N4—Mn2—N1	179.16 (14)	C16—C15—H15A	108.7
O6—Mn2—N3	88.68 (13)	C14—C15—H15B	108.7
O7—Mn2—N3	170.31 (13)	C16—C15—H15B	108.7
N4—Mn2—N3	85.28 (13)	H15A—C15—H15B	107.6
N1—Mn2—N3	95.11 (13)	N1—C16—C15	112.7 (4)
O6—Mn2—N2	176.79 (16)	N1—C16—H16A	109.1
O7—Mn2—N2	95.20 (14)	C15—C16—H16A	109.1
N4—Mn2—N2	90.61 (13)	N1—C16—H16B	109.1
N1—Mn2—N2	88.62 (13)	C15—C16—H16B	109.1
N3—Mn2—N2	94.04 (15)	H16A—C16—H16B	107.8
N6—C1—C2	111.7 (3)	C16—N1—Mn2	119.3 (2)
N6—C1—H1A	109.3	C16—N1—H1C	107.5
C2—C1—H1A	109.3	Mn2—N1—H1C	107.5
N6—C1—H1B	109.3	C16—N1—H1D	107.5
C2—C1—H1B	109.3	Mn2—N1—H1D	107.5
H1A—C1—H1B	107.9	H1C—N1—H1D	107.0
C3—C2—C1	112.9 (3)	C14—N2—Mn2	117.2 (3)
C3—C2—H2A	109.0	C14—N2—H2C	108.0
C1—C2—H2A	109.0	Mn2—N2—H2C	108.0
C3—C2—H2B	109.0	C14—N2—H2D	108.0
C1—C2—H2B	109.0	Mn2—N2—H2D	108.0
H2A—C2—H2B	107.8	H2C—N2—H2D	107.2
C2—C3—N5	114.3 (3)	C9—N3—Mn2	119.5 (2)
C2—C3—H3A	108.7	C9—N3—H3C	107.5
N5—C3—H3A	108.7	Mn2—N3—H3C	107.5
C2—C3—H3B	108.7	C9—N3—H3D	107.5
N5—C3—H3B	108.7	Mn2—N3—H3D	107.5
H3A—C3—H3B	107.6	H3C—N3—H3D	107.0
N8—C4—C5	111.9 (3)	C11—N4—Mn2	117.5 (2)
N8—C4—H4A	109.2	C11—N4—H4C	107.9
C5—C4—H4A	109.2	Mn2—N4—H4C	107.9
N8—C4—H4B	109.2	C11—N4—H4D	107.9
C5—C4—H4B	109.2	Mn2—N4—H4D	107.9
H4A—C4—H4B	107.9	H4C—N4—H4D	107.2
C6—C5—C4	112.7 (3)	C3—N5—Mn1	119.4 (2)
C6—C5—H5A	109.1	C3—N5—H5C	107.5
C4—C5—H5A	109.1	Mn1—N5—H5C	107.5
C6—C5—H5B	109.1	C3—N5—H5D	107.5
C4—C5—H5B	109.1	Mn1—N5—H5D	107.5
H5A—C5—H5B	107.8	H5C—N5—H5D	107.0
C5—C6—N7	113.2 (3)	C1—N6—Mn1	119.3 (2)
C5—C6—H6A	108.9	C1—N6—H6C	107.5
N7—C6—H6A	108.9	Mn1—N6—H6C	107.5
C5—C6—H6B	108.9	C1—N6—H6D	107.5
N7—C6—H6B	108.9	Mn1—N6—H6D	107.5
H6A—C6—H6B	107.7	H6C—N6—H6D	107.0
O3—C7—O2	127.3 (4)	C6—N7—Mn1	115.2 (2)
O3—C7—C8	120.4 (3)	C6—N7—H7A	108.5
O2—C7—C8	112.3 (3)	Mn1—N7—H7A	108.5
O4—C8—O1	125.6 (4)	C6—N7—H7B	108.5
O4—C8—C7	120.2 (3)	Mn1—N7—H7B	108.5
O1—C8—C7	114.2 (3)	H7A—N7—H7B	107.5
C10—C9—N3	112.2 (4)	C4—N8—Mn1	119.4 (2)
C10—C9—H9A	109.2	C4—N8—H8A	107.5
N3—C9—H9A	109.2	Mn1—N8—H8A	107.5
C10—C9—H9B	109.2	C4—N8—H8B	107.5
N3—C9—H9B	109.2	Mn1—N8—H8B	107.5
H9A—C9—H9B	107.9	H8A—N8—H8B	107.0
C9—C10—C11	112.7 (4)	C8—O1—Mn1	116.5 (2)
C9—C10—H10A	109.1	C7—O2—Mn1	115.8 (2)
C11—C10—H10A	109.1	C12—O6—Mn2	115.4 (3)
C9—C10—H10B	109.1	C13—O7—Mn2	113.7 (3)
C11—C10—H10B	109.1	H1W—O9—H2W	112 (5)
H10A—C10—H10B	107.8	H3W—O10—H4W	117 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H3W···Cl2	0.81 (6)	2.70 (7)	3.205 (5)	122 (7)
O10—H4W···O6	0.81 (5)	2.71 (7)	3.078 (5)	110 (5)
O9—H2W···Cl1i	0.83 (3)	2.55 (2)	3.348 (4)	163 (5)
O9—H1W···O10ii	0.82 (5)	2.03 (5)	2.845 (6)	170 (6)
N8—H8B···Cl2i	0.90	2.61	3.366 (3)	142
N8—H8A···O3iii	0.90	2.59	3.426 (4)	154
N7—H7B···O4iii	0.90	2.45	3.195 (4)	141
N7—H7A···O8iv	0.90	2.13	3.014 (4)	169
N6—H6D···O9	0.90	2.20	3.054 (4)	157
N6—H6C···O8iv	0.90	2.21	3.046 (4)	155
N5—H5D···O4iii	0.90	2.04	2.942 (4)	176
N5—H5C···Cl1v	0.90	2.41	3.299 (3)	172
N4—H4D···Cl1vi	0.90	2.53	3.423 (3)	170
N4—H4C···O2vii	0.90	2.42	3.206 (4)	147
N3—H3D···Cl2	0.90	2.25	3.115 (3)	162
N3—H3C···O5viii	0.90	2.02	2.831 (4)	149
N2—H2D···Cl1vi	0.90	2.54	3.317 (4)	144
N2—H2C···O8viii	0.90	2.15	3.024 (5)	163
N1—H1D···Cl2	0.90	2.71	3.404 (3)	135
N1—H1C···Cl1iii	0.90	2.55	3.388 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H3W⋯Cl2	0.81 (6)	2.70 (7)	3.205 (5)	122 (7)
O10—H4W⋯O6	0.81 (5)	2.71 (7)	3.078 (5)	110 (5)
O9—H2W⋯Cl1i	0.83 (3)	2.55 (2)	3.348 (4)	163 (5)
O9—H1W⋯O10ii	0.82 (5)	2.03 (5)	2.845 (6)	170 (6)
N8—H8B⋯Cl2i	0.90	2.61	3.366 (3)	142
N8—H8A⋯O3iii	0.90	2.59	3.426 (4)	154
N7—H7B⋯O4iii	0.90	2.45	3.195 (4)	141
N7—H7A⋯O8iv	0.90	2.13	3.014 (4)	169
N6—H6D⋯O9	0.90	2.20	3.054 (4)	157
N6—H6C⋯O8iv	0.90	2.21	3.046 (4)	155
N5—H5D⋯O4iii	0.90	2.04	2.942 (4)	176
N5—H5C⋯Cl1v	0.90	2.41	3.299 (3)	172
N4—H4D⋯Cl1vi	0.90	2.53	3.423 (3)	170
N4—H4C⋯O2vii	0.90	2.42	3.206 (4)	147
N3—H3D⋯Cl2	0.90	2.25	3.115 (3)	162
N3—H3C⋯O5viii	0.90	2.02	2.831 (4)	149
N2—H2D⋯Cl1vi	0.90	2.54	3.317 (4)	144
N2—H2C⋯O8viii	0.90	2.15	3.024 (5)	163
N1—H1D⋯Cl2	0.90	2.71	3.404 (3)	135
N1—H1C⋯Cl1iii	0.90	2.55	3.388 (3)	155

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