Tetra-μ2-acetato-diaqua­bis­(μ2-2-{[1,3-dihy­droxy-2-(oxidometh­yl)propan-2-yl]imino­meth­yl}phenolato)trimanganese(II,III) acetonitrile disolvate dihydrate

Guo, Y.; Huang, J.; Huang, Y.; Wang, J.; Yu, Y.

doi:10.1107/S1600536811027899

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1098

doi:10.1107/S1600536811027899

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Tetra-μ₂-acetato-diaquabis(μ₂-2-{[1,3-dihydroxy-2-(oxidomethyl)propan-2-yl]iminomethyl}phenolato)trimanganese(II,III) acetonitrile disolvate dihydrate

Yuhua Guo,^a Jianping Huang,^a Yong Huang,^a Junyue Wang ^a and Youzhu Yu ^a ^*

^aDepartment of Chemistry and Environmental Engineering, Anyang Institute of Technology, Henan 455000, People's Republic of China
^*Correspondence e-mail: 119yyz@163.com

(Received 26 June 2011; accepted 12 July 2011; online 16 July 2011)

In the title complex, [Mn^IIMn^III₂(C₁₁H₁₃NO₄)₂(CH₃CO₂)₄(H₂O)₂]·2CH₃CN·2H₂O, there are two Mn^III and one Mn^II atoms. The Mn^II atom lies on an inversion center and the Mn^III—Mn^II—Mn^III angle is therefore 180°, as required by crystallographic symmetry. The Mn^III and Mn^II atoms are six-coordinated in a distorted octahedral geometry. In the crystal, complex molecules and solvent molecules are linked into a three-dimensional network by O—H⋯O and O—H⋯N hydrogen-bonding interactions.

Related literature

For the importance of Mn complexes in magnetism and biomimetics, see: Stamatatos & Christou (2009 ); Ferreira et al. (2004 ). For properties and structures of related compounds, see: Kessissoglou et al. (1992 ); Liu et al. (2010 ).

Experimental

Crystal data

[Mn₃(C₁₁H₁₃NO₄)₂(C₂H₃O₂)₄(H₂O)₂]·2C₂H₃N·2H₂O
M_r = 1001.62
Monoclinic, P 2₁ /c
a = 10.6032 (5) Å
b = 12.2114 (6) Å
c = 19.1608 (9) Å
β = 118.856 (3)°
V = 2172.89 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
53356 measured reflections
5507 independent reflections
3798 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.07
5507 reflections
294 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O10ⁱ	0.85 (1)	1.97 (1)	2.806 (4)	167 (3)
O9—H9B⋯O8ⁱⁱ	0.85 (1)	2.23 (3)	3.008 (3)	153 (5)
O9—H9B⋯O1ⁱⁱ	0.85 (1)	2.61 (3)	3.322 (3)	142 (5)
O10—H10C⋯O5ⁱⁱⁱ	0.85 (1)	2.06 (1)	2.907 (4)	176 (5)
O10—H10D⋯N2^iv	0.85 (1)	2.07 (1)	2.914 (6)	174 (6)
O2—H2⋯O3^v	0.82	2.55	3.362 (5)	172
O3—H3⋯O6^vi	0.82	2.00	2.777 (3)	159
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+1, -z+2; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027899/pv2425sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027899/pv2425Isup2.hkl

checkCIF report

Comment top

The fascination of inorganic chemists with Mn coordination chemistry over the last two decades or so has been primarily driven by the relevance of Mn-complexes to magnetic and biomimetic fields (Stamatatos & Christou, 2009; Ferreira et al.2004). As a contribution to these fields, we report here the synthesis and crystal structure of the title compound.

In the title complex (Fig. 1), the Mn^III and Mn^II atoms are six-coordinated in a distorted octahedral geometry and the two Mn^III are in the same coordination environment. The Mn(II) lies on an inversion center, therefore, the angle Mn(III)-Mn(II)—Mn(III) is 180° as required by crystallographic symmetry. The bond lengths and bond angles in the title complex are comparable with those observed in the related complexes (Kessissoglou et al., 1992). In the crystal structure, the complex molecules and the solvent molecules are linked through intermolecular O—H···O and O—H···N hydrogen bonds (Table 1) into a three-dimensional network.

Related literature top

For the importance of Mn complexes in magnetism and biomimetics, see: Stamatatos & Christou (2009); Ferreira et al. (2004). For properties and structures of related compounds, see: Kessissoglou et al. (1992); Liu et al. (2010).

Experimental top

To a stirred acetonitrile (20 ml) solution of H₂SALATHM (1 mmol, 225 mg) was added Mn(OAc)₂.4H₂O (1 mmol, 245 mg). The resulting dark-red solution was stirred for 1 h and the filtrate was allowed to stand at room temperature for about three days, whereupon dark block crystal suitable for X-ray diffraction analysis was obtained.

Computing details top

Data collection: APEX2 (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.

Tetra-µ₂-acetato-diaquabis(µ₂-2-{[1,3-dihydroxy-2- (oxidomethyl)propan-2-yl]iminomethyl}phenolato)trimanganese(II,III) acetonitrile disolvate dihydrate top

Crystal data top

[Mn₃(C₁₁H₁₃NO₄)₂(C₂H₃O₂)₄(H₂O)₂]·2C₂H₃N·2H₂O	F(000) = 1038
M_r = 1001.62	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9948 reflections
a = 10.6032 (5) Å	θ = 2.4–28.4°
b = 12.2114 (6) Å	µ = 0.94 mm⁻¹
c = 19.1608 (9) Å	T = 293 K
β = 118.856 (3)°	Block, black
V = 2172.89 (18) Å³	0.20 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.086
Graphite monochromator	θ_max = 28.6°, θ_min = 2.1°
ϕ and ω scans	h = −14→14
53356 measured reflections	k = −16→16
5507 independent reflections	l = −25→25

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0525P)² + 2.7933P] where P = (F_o² + 2F_c²)/3
5507 reflections	(Δ/σ)_max = 0.024
294 parameters	Δρ_max = 0.72 e Å⁻³
7 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Mn₃(C₁₁H₁₃NO₄)₂(C₂H₃O₂)₄(H₂O)₂]·2C₂H₃N·2H₂O	V = 2172.89 (18) Å³
M_r = 1001.62	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6032 (5) Å	µ = 0.94 mm⁻¹
b = 12.2114 (6) Å	T = 293 K
c = 19.1608 (9) Å	0.20 × 0.20 × 0.20 mm
β = 118.856 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3798 reflections with I > 2σ(I)
53356 measured reflections	R_int = 0.086
5507 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	7 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.72 e Å⁻³
5507 reflections	Δρ_min = −0.61 e Å⁻³
294 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.1569 (3)	0.8511 (2)	0.84008 (18)	0.0317 (6)
C2	−0.2687 (4)	0.8090 (3)	0.8512 (2)	0.0419 (8)
H2A	−0.2506	0.7888	0.9020	0.050*
C3	−0.4053 (4)	0.7971 (3)	0.7877 (2)	0.0548 (10)
H3A	−0.4788	0.7710	0.7966	0.066*
C4	−0.4352 (4)	0.8235 (4)	0.7105 (3)	0.0604 (11)
H4	−0.5274	0.8140	0.6680	0.072*
C5	−0.3275 (4)	0.8635 (3)	0.6980 (2)	0.0475 (9)
H5	−0.3469	0.8808	0.6465	0.057*
C6	−0.1874 (3)	0.8789 (2)	0.76201 (18)	0.0345 (7)
C7	−0.0836 (3)	0.9291 (2)	0.74451 (18)	0.0334 (6)
H7	−0.1103	0.9400	0.6911	0.040*
C9	0.1393 (3)	1.0157 (3)	0.77120 (18)	0.0352 (7)
C10	0.0585 (4)	1.0849 (3)	0.6962 (2)	0.0464 (9)
H10A	0.1265	1.1269	0.6868	0.056*
H10B	0.0049	1.0376	0.6506	0.056*
C11	0.2297 (4)	0.9275 (3)	0.7590 (2)	0.0486 (9)
H11A	0.2880	0.9621	0.7388	0.058*
H11B	0.2946	0.8953	0.8102	0.058*
C12	0.2357 (3)	1.0870 (3)	0.84214 (18)	0.0342 (7)
H12A	0.3199	1.1091	0.8382	0.041*
H12B	0.1840	1.1525	0.8422	0.041*
C13	0.3707 (3)	0.7594 (2)	0.94069 (19)	0.0357 (7)
C14	0.3997 (5)	0.6436 (3)	0.9255 (4)	0.0821 (17)
H14A	0.4021	0.6404	0.8761	0.123*
H14B	0.3248	0.5965	0.9226	0.123*
H14C	0.4907	0.6200	0.9682	0.123*
C15	0.3292 (3)	0.9424 (2)	1.09183 (17)	0.0315 (6)
C16	0.3403 (4)	0.9114 (3)	1.1703 (2)	0.0440 (8)
H16A	0.4374	0.9225	1.2120	0.066*
H16B	0.3147	0.8358	1.1690	0.066*
H16C	0.2761	0.9561	1.1801	0.066*
C17	0.1100 (6)	0.8401 (4)	0.5308 (3)	0.0706 (13)
H17B	0.0142	0.8391	0.4864	0.106*
H17A	0.1057	0.8323	0.5794	0.106*
H17C	0.1644	0.7806	0.5258	0.106*
C18	0.1775 (5)	0.9407 (4)	0.5317 (3)	0.0742 (14)
H9A	0.082 (4)	1.158 (2)	0.938 (3)	0.111*
H9B	−0.014 (5)	1.099 (3)	0.953 (3)	0.111*
H10C	0.320 (2)	0.242 (4)	0.984 (3)	0.111*
H10D	0.235 (5)	0.327 (3)	0.987 (3)	0.111*
N1	0.0433 (3)	0.9604 (2)	0.79651 (14)	0.0299 (5)
N2	0.2282 (7)	1.0199 (4)	0.5303 (5)	0.146 (3)
O1	−0.0288 (2)	0.86304 (18)	0.90298 (12)	0.0356 (5)
O2	0.1473 (4)	0.8430 (3)	0.7059 (2)	0.0775 (9)
H2	0.1298	0.7957	0.7305	0.116*
O3	−0.0374 (3)	1.1568 (2)	0.70565 (16)	0.0569 (7)
H3	−0.0849	1.1909	0.6642	0.085*
O4	0.2792 (2)	1.02733 (16)	0.91436 (11)	0.0290 (4)
O5	0.4759 (2)	0.82092 (18)	0.97622 (15)	0.0466 (6)
O6	0.2412 (2)	0.78562 (16)	0.91590 (13)	0.0359 (5)
O7	0.4363 (2)	0.9780 (2)	1.08976 (14)	0.0480 (6)
O8	0.2062 (2)	0.92758 (18)	1.03081 (12)	0.0358 (5)
O9	0.0281 (3)	1.10148 (19)	0.92495 (16)	0.0451 (6)
O10	0.2353 (3)	0.2668 (3)	0.9640 (2)	0.0640 (8)
Mn1	0.13180 (4)	0.94343 (3)	0.91490 (2)	0.02691 (13)
Mn2	0.5000	1.0000	1.0000	0.02878 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0261 (14)	0.0260 (14)	0.0358 (16)	−0.0014 (11)	0.0091 (12)	−0.0011 (11)
C2	0.0379 (17)	0.0424 (18)	0.0430 (19)	−0.0061 (14)	0.0176 (15)	0.0013 (14)
C3	0.0326 (17)	0.061 (2)	0.064 (3)	−0.0180 (17)	0.0181 (17)	−0.0055 (19)
C4	0.0317 (18)	0.069 (3)	0.057 (2)	−0.0176 (18)	0.0032 (17)	−0.003 (2)
C5	0.0363 (18)	0.050 (2)	0.0377 (19)	−0.0101 (15)	0.0030 (14)	−0.0016 (15)
C6	0.0258 (14)	0.0306 (15)	0.0382 (17)	−0.0024 (12)	0.0085 (12)	−0.0031 (12)
C7	0.0313 (15)	0.0351 (16)	0.0260 (14)	0.0012 (12)	0.0075 (12)	0.0006 (12)
C9	0.0302 (15)	0.0398 (16)	0.0328 (16)	−0.0026 (13)	0.0129 (13)	0.0056 (13)
C10	0.0397 (18)	0.055 (2)	0.0352 (18)	−0.0057 (16)	0.0104 (15)	0.0132 (15)
C11	0.049 (2)	0.059 (2)	0.042 (2)	0.0034 (17)	0.0253 (17)	−0.0003 (16)
C12	0.0273 (14)	0.0342 (15)	0.0340 (16)	−0.0017 (12)	0.0092 (12)	0.0082 (12)
C13	0.0308 (15)	0.0274 (14)	0.0443 (18)	−0.0002 (12)	0.0145 (14)	−0.0049 (13)
C14	0.045 (2)	0.040 (2)	0.139 (5)	0.0000 (17)	0.026 (3)	−0.030 (3)
C15	0.0321 (15)	0.0281 (14)	0.0313 (15)	0.0043 (12)	0.0130 (12)	−0.0022 (12)
C16	0.0445 (19)	0.0471 (19)	0.0348 (18)	0.0055 (15)	0.0148 (15)	0.0028 (14)
C17	0.102 (4)	0.049 (2)	0.069 (3)	−0.006 (2)	0.047 (3)	−0.004 (2)
C18	0.074 (3)	0.047 (2)	0.087 (3)	0.001 (2)	0.027 (3)	0.011 (2)
N1	0.0262 (12)	0.0323 (13)	0.0284 (12)	−0.0012 (10)	0.0110 (10)	0.0024 (10)
N2	0.124 (5)	0.065 (3)	0.225 (8)	−0.021 (3)	0.065 (5)	0.031 (4)
O1	0.0247 (10)	0.0422 (12)	0.0327 (11)	−0.0046 (9)	0.0080 (9)	0.0057 (9)
O2	0.101 (3)	0.072 (2)	0.068 (2)	−0.0063 (19)	0.047 (2)	−0.0187 (17)
O3	0.0442 (14)	0.0612 (17)	0.0493 (15)	0.0126 (12)	0.0099 (12)	0.0258 (13)
O4	0.0218 (9)	0.0311 (10)	0.0286 (10)	0.0003 (8)	0.0078 (8)	0.0061 (8)
O5	0.0310 (11)	0.0290 (11)	0.0633 (16)	−0.0016 (9)	0.0096 (11)	−0.0065 (11)
O6	0.0285 (10)	0.0283 (10)	0.0440 (13)	−0.0011 (8)	0.0120 (9)	−0.0063 (9)
O7	0.0313 (12)	0.0740 (17)	0.0372 (13)	−0.0035 (12)	0.0152 (10)	−0.0003 (12)
O8	0.0306 (11)	0.0434 (12)	0.0291 (11)	−0.0049 (9)	0.0109 (9)	−0.0004 (9)
O9	0.0436 (14)	0.0384 (13)	0.0596 (16)	0.0039 (10)	0.0299 (12)	−0.0016 (11)
O10	0.0495 (16)	0.0581 (18)	0.081 (2)	0.0004 (13)	0.0286 (16)	−0.0148 (15)
Mn1	0.0215 (2)	0.0281 (2)	0.0258 (2)	−0.00170 (16)	0.00718 (17)	0.00117 (17)
Mn2	0.0204 (3)	0.0280 (3)	0.0314 (3)	−0.0005 (2)	0.0073 (2)	−0.0008 (2)

Geometric parameters (Å, º) top

C1—O1	1.319 (3)	C14—H14B	0.9600
C1—C2	1.400 (4)	C14—H14C	0.9600
C1—C6	1.411 (4)	C15—O7	1.234 (4)
C2—C3	1.378 (5)	C15—O8	1.276 (3)
C2—H2A	0.9300	C15—C16	1.498 (4)
C3—C4	1.393 (6)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.365 (5)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18	1.418 (6)
C5—C6	1.410 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.434 (4)	C17—H17C	0.9600
C7—N1	1.287 (4)	C18—N2	1.113 (6)
C7—H7	0.9300	N1—Mn1	2.004 (2)
C9—N1	1.484 (4)	O1—Mn1	1.882 (2)
C9—C12	1.520 (4)	O2—H2	0.8200
C9—C10	1.525 (4)	O3—H3	0.8200
C9—C11	1.533 (5)	O4—Mn1	1.8729 (19)
C10—O3	1.420 (5)	O4—Mn2	2.1395 (18)
C10—H10A	0.9700	O5—Mn2	2.223 (2)
C10—H10B	0.9700	O6—Mn1	2.244 (2)
C11—O2	1.416 (5)	O7—Mn2	2.147 (2)
C11—H11A	0.9700	O8—Mn1	1.975 (2)
C11—H11B	0.9700	O9—Mn1	2.275 (2)
C12—O4	1.429 (3)	O9—H9A	0.851 (10)
C12—H12A	0.9700	O9—H9B	0.851 (10)
C12—H12B	0.9700	O10—H10C	0.851 (10)
C13—O5	1.241 (4)	O10—H10D	0.849 (10)
C13—O6	1.258 (4)	Mn2—O4ⁱ	2.1395 (18)
C13—C14	1.505 (5)	Mn2—O7ⁱ	2.147 (2)
C14—H14A	0.9600	Mn2—O5ⁱ	2.223 (2)

O1—C1—C2	118.4 (3)	H16A—C16—H16B	109.5
O1—C1—C6	123.4 (3)	C15—C16—H16C	109.5
C2—C1—C6	118.2 (3)	H16A—C16—H16C	109.5
C3—C2—C1	120.7 (3)	H16B—C16—H16C	109.5
C3—C2—H2A	119.7	C18—C17—H17B	109.5
C1—C2—H2A	119.7	C18—C17—H17A	109.5
C2—C3—C4	121.1 (3)	H17B—C17—H17A	109.5
C2—C3—H3A	119.4	C18—C17—H17C	109.5
C4—C3—H3A	119.4	H17B—C17—H17C	109.5
C5—C4—C3	119.3 (3)	H17A—C17—H17C	109.5
C5—C4—H4	120.4	N2—C18—C17	178.1 (7)
C3—C4—H4	120.4	C7—N1—C9	120.5 (3)
C4—C5—C6	120.9 (3)	C7—N1—Mn1	126.1 (2)
C4—C5—H5	119.6	C9—N1—Mn1	113.37 (18)
C6—C5—H5	119.6	C1—O1—Mn1	129.90 (19)
C5—C6—C1	119.8 (3)	C11—O2—H2	109.5
C5—C6—C7	117.3 (3)	C10—O3—H3	109.5
C1—C6—C7	122.8 (3)	C12—O4—Mn1	113.83 (16)
N1—C7—C6	125.4 (3)	C12—O4—Mn2	122.99 (17)
N1—C7—H7	117.3	Mn1—O4—Mn2	121.17 (9)
C6—C7—H7	117.3	C13—O5—Mn2	133.8 (2)
N1—C9—C12	103.9 (2)	C13—O6—Mn1	133.38 (19)
N1—C9—C10	113.5 (3)	C15—O7—Mn2	136.1 (2)
C12—C9—C10	110.8 (3)	C15—O8—Mn1	133.9 (2)
N1—C9—C11	108.0 (3)	Mn1—O9—H9A	116 (2)
C12—C9—C11	109.8 (3)	Mn1—O9—H9B	116 (3)
C10—C9—C11	110.7 (3)	H9A—O9—H9B	109 (2)
O3—C10—C9	109.5 (3)	H10C—O10—H10D	110 (3)
O3—C10—H10A	109.8	O4—Mn1—O1	173.45 (9)
C9—C10—H10A	109.8	O4—Mn1—O8	100.27 (9)
O3—C10—H10B	109.8	O1—Mn1—O8	86.11 (9)
C9—C10—H10B	109.8	O4—Mn1—N1	82.72 (9)
H10A—C10—H10B	108.2	O1—Mn1—N1	90.84 (9)
O2—C11—C9	114.0 (3)	O8—Mn1—N1	176.23 (10)
O2—C11—H11A	108.8	O4—Mn1—O6	92.33 (8)
C9—C11—H11A	108.8	O1—Mn1—O6	89.24 (9)
O2—C11—H11B	108.8	O8—Mn1—O6	88.97 (9)
C9—C11—H11B	108.8	N1—Mn1—O6	93.22 (9)
H11A—C11—H11B	107.6	O4—Mn1—O9	88.58 (9)
O4—C12—C9	109.7 (2)	O1—Mn1—O9	90.39 (9)
O4—C12—H12A	109.7	O8—Mn1—O9	86.27 (9)
C9—C12—H12A	109.7	N1—Mn1—O9	91.54 (10)
O4—C12—H12B	109.7	O6—Mn1—O9	175.23 (9)
C9—C12—H12B	109.7	O4ⁱ—Mn2—O4	180.000 (1)
H12A—C12—H12B	108.2	O4ⁱ—Mn2—O7ⁱ	89.03 (8)
O5—C13—O6	125.6 (3)	O4—Mn2—O7ⁱ	90.98 (8)
O5—C13—C14	117.5 (3)	O4ⁱ—Mn2—O7	90.97 (8)
O6—C13—C14	117.0 (3)	O4—Mn2—O7	89.02 (8)
C13—C14—H14A	109.5	O7ⁱ—Mn2—O7	180.000 (1)
C13—C14—H14B	109.5	O4ⁱ—Mn2—O5	88.78 (8)
H14A—C14—H14B	109.5	O4—Mn2—O5	91.22 (8)
C13—C14—H14C	109.5	O7ⁱ—Mn2—O5	90.48 (10)
H14A—C14—H14C	109.5	O7—Mn2—O5	89.52 (10)
H14B—C14—H14C	109.5	O4ⁱ—Mn2—O5ⁱ	91.22 (8)
O7—C15—O8	124.7 (3)	O4—Mn2—O5ⁱ	88.78 (8)
O7—C15—C16	119.5 (3)	O7ⁱ—Mn2—O5ⁱ	89.52 (10)
O8—C15—C16	115.7 (3)	O7—Mn2—O5ⁱ	90.48 (10)
C15—C16—H16A	109.5	O5—Mn2—O5ⁱ	180.000 (1)
C15—C16—H16B	109.5

O1—C1—C2—C3	178.6 (3)	Mn2—O4—Mn1—O6	−51.58 (12)
C6—C1—C2—C3	−1.2 (5)	C12—O4—Mn1—O9	−71.9 (2)
C1—C2—C3—C4	1.9 (6)	Mn2—O4—Mn1—O9	123.73 (12)
C2—C3—C4—C5	−1.1 (7)	C1—O1—Mn1—O4	−2.9 (10)
C3—C4—C5—C6	−0.4 (6)	C1—O1—Mn1—O8	164.2 (3)
C4—C5—C6—C1	1.0 (5)	C1—O1—Mn1—N1	−13.6 (3)
C4—C5—C6—C7	−175.3 (4)	C1—O1—Mn1—O6	−106.8 (3)
O1—C1—C6—C5	180.0 (3)	C1—O1—Mn1—O9	78.0 (3)
C2—C1—C6—C5	−0.2 (5)	C15—O8—Mn1—O4	−15.7 (3)
O1—C1—C6—C7	−3.9 (5)	C15—O8—Mn1—O1	165.8 (3)
C2—C1—C6—C7	175.9 (3)	C15—O8—Mn1—N1	−158.1 (13)
C5—C6—C7—N1	171.7 (3)	C15—O8—Mn1—O6	76.5 (3)
C1—C6—C7—N1	−4.5 (5)	C15—O8—Mn1—O9	−103.6 (3)
N1—C9—C10—O3	51.4 (4)	C7—N1—Mn1—O4	−173.7 (3)
C12—C9—C10—O3	−65.0 (3)	C9—N1—Mn1—O4	5.8 (2)
C11—C9—C10—O3	173.0 (3)	C7—N1—Mn1—O1	5.1 (3)
N1—C9—C11—O2	54.4 (4)	C9—N1—Mn1—O1	−175.4 (2)
C12—C9—C11—O2	167.1 (3)	C7—N1—Mn1—O8	−30.9 (16)
C10—C9—C11—O2	−70.3 (4)	C9—N1—Mn1—O8	148.6 (14)
N1—C9—C12—O4	42.2 (3)	C7—N1—Mn1—O6	94.4 (3)
C10—C9—C12—O4	164.4 (3)	C9—N1—Mn1—O6	−86.1 (2)
C11—C9—C12—O4	−73.1 (3)	C7—N1—Mn1—O9	−85.3 (3)
C6—C7—N1—C9	−177.5 (3)	C9—N1—Mn1—O9	94.2 (2)
C6—C7—N1—Mn1	1.9 (4)	C13—O6—Mn1—O4	26.9 (3)
C12—C9—N1—C7	152.4 (3)	C13—O6—Mn1—O1	−159.5 (3)
C10—C9—N1—C7	32.1 (4)	C13—O6—Mn1—O8	−73.4 (3)
C11—C9—N1—C7	−91.0 (3)	C13—O6—Mn1—N1	109.7 (3)
C12—C9—N1—Mn1	−27.1 (3)	C13—O6—Mn1—O9	−74.0 (11)
C10—C9—N1—Mn1	−147.4 (2)	C12—O4—Mn2—O4ⁱ	150 (48)
C11—C9—N1—Mn1	89.5 (3)	Mn1—O4—Mn2—O4ⁱ	−47 (48)
C2—C1—O1—Mn1	−164.9 (2)	C12—O4—Mn2—O7ⁱ	−23.4 (2)
C6—C1—O1—Mn1	14.9 (4)	Mn1—O4—Mn2—O7ⁱ	139.47 (13)
C9—C12—O4—Mn1	−41.2 (3)	C12—O4—Mn2—O7	156.6 (2)
C9—C12—O4—Mn2	122.8 (2)	Mn1—O4—Mn2—O7	−40.53 (13)
O6—C13—O5—Mn2	−9.9 (6)	C12—O4—Mn2—O5	−113.9 (2)
C14—C13—O5—Mn2	169.9 (3)	Mn1—O4—Mn2—O5	48.97 (13)
O5—C13—O6—Mn1	3.4 (5)	C12—O4—Mn2—O5ⁱ	66.1 (2)
C14—C13—O6—Mn1	−176.4 (3)	Mn1—O4—Mn2—O5ⁱ	−131.03 (13)
O8—C15—O7—Mn2	−15.7 (5)	C15—O7—Mn2—O4ⁱ	−148.5 (3)
C16—C15—O7—Mn2	163.0 (2)	C15—O7—Mn2—O4	31.5 (3)
O7—C15—O8—Mn1	3.5 (5)	C15—O7—Mn2—O7ⁱ	112 (100)
C16—C15—O8—Mn1	−175.3 (2)	C15—O7—Mn2—O5	−59.7 (3)
C12—O4—Mn1—O1	9.0 (9)	C15—O7—Mn2—O5ⁱ	120.3 (3)
Mn2—O4—Mn1—O1	−155.3 (8)	C13—O5—Mn2—O4ⁱ	166.7 (3)
C12—O4—Mn1—O8	−157.9 (2)	C13—O5—Mn2—O4	−13.3 (3)
Mn2—O4—Mn1—O8	37.79 (13)	C13—O5—Mn2—O7ⁱ	−104.3 (3)
C12—O4—Mn1—N1	19.8 (2)	C13—O5—Mn2—O7	75.7 (3)
Mn2—O4—Mn1—N1	−144.53 (13)	C13—O5—Mn2—O5ⁱ	30 (100)
C12—O4—Mn1—O6	112.8 (2)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O10ⁱⁱ	0.85 (1)	1.97 (1)	2.806 (4)	167 (3)
O9—H9B···O8ⁱⁱⁱ	0.85 (1)	2.23 (3)	3.008 (3)	153 (5)
O9—H9B···O1ⁱⁱⁱ	0.85 (1)	2.61 (3)	3.322 (3)	142 (5)
O10—H10C···O5^iv	0.85 (1)	2.06 (1)	2.907 (4)	176 (5)
O10—H10D···N2^v	0.85 (1)	2.07 (1)	2.914 (6)	174 (6)
O2—H2···O3^vi	0.82	2.55	3.362 (5)	172
O3—H3···O6^vii	0.82	2.00	2.777 (3)	159

Symmetry codes: (ii) x, y+1, z; (iii) −x, −y+2, −z+2; (iv) −x+1, −y+1, −z+2; (v) x, −y+3/2, z+1/2; (vi) −x, y−1/2, −z+3/2; (vii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Mn₃(C₁₁H₁₃NO₄)₂(C₂H₃O₂)₄(H₂O)₂]·2C₂H₃N·2H₂O
M_r	1001.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.6032 (5), 12.2114 (6), 19.1608 (9)
β (°)	118.856 (3)
V (Å³)	2172.89 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	53356, 5507, 3798
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.07
No. of reflections	5507
No. of parameters	294
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.61

Computer programs: APEX2 (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O10ⁱ	0.851 (10)	1.971 (13)	2.806 (4)	167 (3)
O9—H9B···O8ⁱⁱ	0.851 (10)	2.23 (3)	3.008 (3)	153 (5)
O9—H9B···O1ⁱⁱ	0.851 (10)	2.61 (3)	3.322 (3)	142 (5)
O10—H10C···O5ⁱⁱⁱ	0.851 (10)	2.058 (11)	2.907 (4)	176 (5)
O10—H10D···N2^iv	0.849 (10)	2.068 (13)	2.914 (6)	174 (6)
O2—H2···O3^v	0.82	2.55	3.362 (5)	171.7
O3—H3···O6^vi	0.82	2.00	2.777 (3)	158.9

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+1, −z+2; (iv) x, −y+3/2, z+1/2; (v) −x, y−1/2, −z+3/2; (vi) −x, y+1/2, −z+3/2.

Acknowledgements

This work was supported by the Second Young-Aged Backbone Teachers Foundation of Anyang Institute of Technology.

References

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