Poly[tetra­kis[μ2-1,3-bis­(4-pyrid­yl)propane-κ2N:N′]dichloridobis(phenyl­acetato)dimanganese(II)]

Liu, J.-Y.; Xu, W.

doi:10.1107/S1600536810003466

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m246

doi:10.1107/S1600536810003466

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Poly[tetrakis[μ₂-1,3-bis(4-pyridyl)propane-κ²N:N′]dichloridobis(phenylacetato)dimanganese(II)]

Ji-Yong Liu ^a and Wei Xu ^a ^*

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: xuwei@nbu.edu.cn

(Received 12 January 2010; accepted 28 January 2010; online 3 February 2010)

In the title compound, [Mn₂(C₈H₇O₂)₂Cl₂(C₁₃H₁₄N₂)₄]_n, the two Mn^II atoms lie on inversion centers and are connected by the N-heterocyclic ligands into a wave-like lamellar framework structure. One Mn^II atom is covalently bonded to two Cl atoms and the other to two benzylacetate anions; both Mn atoms show distorted octahedral coordinations.

Related literature

For general background to the use of poly-pyridyl ligand linkers such as 4,4′-bipyridine in the rational design and assembly of coordination polymers, see: Biradha et al. (2006 ). For related structures, see: Carlucci et al. (2002 ).

Experimental

Crystal data

[Mn₂(C₈H₇O₂)₂Cl₂(C₁₃H₁₄N₂)₄]
M_r = 1244.10
Triclinic, $[P \overline 1]$
a = 9.5594 (5) Å
b = 13.0091 (6) Å
c = 13.8484 (6) Å
α = 69.202 (4)°
β = 86.318 (4)°
γ = 69.910 (5)°
V = 1508.74 (13) Å³
Z = 1
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.48 × 0.46 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.77, T_max = 0.88
10180 measured reflections
5303 independent reflections
4041 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.069
S = 0.96
5303 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003466/ng2721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003466/ng2721Isup2.hkl

checkCIF report

Comment top

Over the past few decades, Some poly-pyridyl ligand linkers such as 4,4'-bipyridine have been extensively studied for rational design and assembly of coordination polymers [Biradha et al. (2006)]. However, few studies have been done to 1,3-bis(4-pyridyl)propane (bpp), which has analogous structures to 4,4'-bipyridine ligands. In this paper, we report the synthesis and crystal structure of the title compound.

The molecular unit consists of two Mn²⁺ ions (namely Mn1 and Mn2), four bpp molecules, two phenylacetate anions and two Cl^- anions. The Mn1 and Mn2 atoms both sit at symmetry inversion centers. Each Mn1 atom is coordinated by four N atoms from different bpp ligands and two two oxygen atoms of monodentate phenylacetate ligands to form a MnN₄O₂ chromophore with oxygen atoms occupied the axial positions. The coordination environment of Mn2 is completed by four N atoms and two Cl^- anions, forming a MnN₄Cl₂ chromophore, whose axial positions defined by Cl^- anions. The coordination environment of each Mn(II) could be best describes as distorted octahedral geometry, and the slight distortion is reflected on the cisoid angles [84.37 (5)-95.63 (5)°].

It's noting that the flexible bpp ligands presents two different conformations [Carlucci et al. (2002)], with rational N···N distance 9.223Å for TG bpp [torsion angles of 66.1 (4) and 174.1 (4)°] and 8.091Å for GG' bpp [torsion angles of 75.9 (5) and 163.7 (4)°], which lead to different distances of the adjacent Mn1 and Mn2 (13.065 and 10.930 Å). The Mn1 and Mn2 atoms are connected by bpp ligands into a wave-like lamellar framework structure in rectangle (4, 4) topology (Fig.2), which is further stacked into a 3D supramolecular architecture linked by the C—H···O and C—H···Cl hydrogen bonding interactions.

Related literature top

For general background to the use of poly-pyridyl ligand linkers such as 4,4'-bipyridine in the rational design and assembly of coordination polymers, see: Biradha et al. (2006). For related structures, see: Carlucci et al. (2002).

Experimental top

A mixture of MnCl₂.4H₂O (0.1977 g, 1.00 mmol) with phenylacetic acid (0.2731 g, 2.00 mmol), 1,3-bis(4-pyridyl)propane (0.1976 g, 1.00 mmol) and NaOH (0.0805 g, 2.00 mmol), in the molar ratio 1:2:1:2, and water (10 ml) was placed in a Parr Teflonlined stainless steel vessel (25 ml); the vessel was sealed and heated to 433 K for 3 d, and the reaction mixture was cooled to room temperature, yellow crystals were obtained from the filtrate after a few days.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP view of the title compound. The dispalcement ellipsoids are drawn at 30% probability level [Symmetry codes: (#1) -x + 2, -y + 2, -z +1; (#2) -x + 1, -y + 1, -z; (#3) -x + 2, -y + 1, -z; (#4) x - 1, y, z; (#5) x + 1, y, z].
	Fig. 2. The two-dimensional layer of the compound. Hydrogen atoms are omitted for clarity.

Poly[tetrakis[µ₂-1,3-bis(4-pyridyl)propane- κ²N:N']dichloridobis(phenylacetato)dimanganese(II)] top

Crystal data top

[Mn₂(C₈H₇O₂)₂Cl₂(C₁₃H₁₄N₂)₄]	Z = 1
M_r = 1244.10	F(000) = 650
Triclinic, P1	D_x = 1.369 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5594 (5) Å	Cell parameters from 5358 reflections
b = 13.0091 (6) Å	θ = 3.3–29.3°
c = 13.8484 (6) Å	µ = 0.56 mm⁻¹
α = 69.202 (4)°	T = 293 K
β = 86.318 (4)°	Block, yellow
γ = 69.910 (5)°	0.48 × 0.46 × 0.23 mm
V = 1508.74 (13) Å³

Data collection top

Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer	5303 independent reflections
Radiation source: fine-focus sealed tube	4041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 10.3592 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −13→15
T_min = 0.77, T_max = 0.88	l = −16→16
10180 measured reflections

Refinement top

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
5303 reflections	Δρ_max = 0.23 e Å⁻³
383 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (8)

Crystal data top

[Mn₂(C₈H₇O₂)₂Cl₂(C₁₃H₁₄N₂)₄]	γ = 69.910 (5)°
M_r = 1244.10	V = 1508.74 (13) Å³
Triclinic, P1	Z = 1
a = 9.5594 (5) Å	Mo Kα radiation
b = 13.0091 (6) Å	µ = 0.56 mm⁻¹
c = 13.8484 (6) Å	T = 293 K
α = 69.202 (4)°	0.48 × 0.46 × 0.23 mm
β = 86.318 (4)°

Data collection top

Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer	5303 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	4041 reflections with I > 2σ(I)
T_min = 0.77, T_max = 0.88	R_int = 0.021
10180 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 0.96	Δρ_max = 0.23 e Å⁻³
5303 reflections	Δρ_min = −0.19 e Å⁻³
383 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

	x	y	z	U_iso*/U_eq
Mn1	1.0000	1.0000	0.5000	0.02534 (11)
Mn2	0.5000	0.5000	0.0000	0.02969 (12)
Cl	0.34313 (5)	0.44105 (5)	0.14744 (4)	0.04018 (14)
O1	0.75819 (12)	1.08965 (11)	0.46913 (9)	0.0362 (3)
O2	0.64269 (15)	1.08883 (14)	0.33545 (10)	0.0522 (4)
N1	1.00849 (15)	0.85804 (12)	0.42979 (11)	0.0288 (3)
N2	0.69038 (16)	0.45962 (13)	0.12058 (11)	0.0312 (4)
N3	1.05314 (16)	1.09985 (13)	0.33750 (11)	0.0299 (3)
N4	1.40150 (16)	0.69381 (14)	−0.00685 (12)	0.0352 (4)
C1	1.1512 (2)	0.71106 (18)	0.36191 (16)	0.0417 (5)
H1	1.2449	0.6678	0.3479	0.050*
C2	1.1387 (2)	0.79193 (18)	0.40728 (15)	0.0396 (5)
H2	1.2256	0.8012	0.4232	0.047*
C3	0.8877 (2)	0.84106 (17)	0.40593 (15)	0.0383 (5)
H3	0.7952	0.8851	0.4207	0.046*
C4	0.8926 (2)	0.76112 (18)	0.36018 (16)	0.0412 (5)
H4	0.8043	0.7531	0.3450	0.049*
C5	1.0260 (2)	0.69363 (16)	0.33697 (14)	0.0313 (4)
C6	1.0345 (2)	0.60283 (17)	0.29095 (15)	0.0380 (5)
H6B	1.1264	0.5864	0.2560	0.046*
H6A	0.9517	0.6335	0.2398	0.046*
C7	1.0295 (2)	0.49008 (16)	0.37315 (14)	0.0334 (4)
H7A	0.9340	0.5064	0.4039	0.040*
H7B	1.1066	0.4643	0.4273	0.040*
C8	1.0510 (2)	0.38992 (16)	0.33360 (14)	0.0324 (4)
H8B	1.1438	0.3762	0.2993	0.039*
H8A	1.0597	0.3191	0.3923	0.039*
C9	0.92566 (19)	0.41373 (15)	0.25951 (13)	0.0282 (4)
C10	0.9306 (2)	0.46458 (17)	0.15395 (14)	0.0349 (5)
H10	1.0132	0.4847	0.1270	0.042*
C11	0.8136 (2)	0.48548 (17)	0.08854 (14)	0.0357 (5)
H11	0.8204	0.5197	0.0178	0.043*
C12	0.6865 (2)	0.40978 (17)	0.22292 (15)	0.0379 (5)
H12	0.6029	0.3901	0.2480	0.045*
C13	0.7992 (2)	0.38592 (17)	0.29348 (14)	0.0368 (5)
H13	0.7904	0.3511	0.3639	0.044*
C14	1.0025 (2)	1.17152 (17)	0.15429 (14)	0.0367 (5)
H14	0.9354	1.1924	0.0991	0.044*
C15	0.9625 (2)	1.13025 (16)	0.25450 (14)	0.0339 (4)
H15	0.8686	1.1232	0.2649	0.041*
C16	1.1850 (2)	1.11445 (17)	0.31863 (15)	0.0354 (5)
H16	1.2483	1.0968	0.3749	0.043*
C17	1.2331 (2)	1.15408 (17)	0.22097 (15)	0.0391 (5)
H17	1.3266	1.1620	0.2126	0.047*
C18	1.1416 (2)	1.18203 (16)	0.13546 (15)	0.0352 (5)
C19	1.1965 (3)	1.21582 (18)	0.02808 (16)	0.0487 (6)
H19B	1.2622	1.2595	0.0242	0.058*
H19A	1.1122	1.2661	−0.0217	0.058*
C20	1.2812 (2)	1.10655 (19)	0.00013 (17)	0.0507 (6)
H20B	1.3367	1.1287	−0.0602	0.061*
H20A	1.3523	1.0496	0.0570	0.061*
C21	1.1775 (3)	1.0502 (2)	−0.02233 (18)	0.0550 (6)
H21A	1.1016	1.0501	0.0277	0.066*
H21B	1.1275	1.0973	−0.0905	0.066*
C22	1.2571 (2)	0.92665 (19)	−0.01826 (16)	0.0416 (5)
C23	1.3214 (2)	0.89998 (18)	−0.10331 (15)	0.0417 (5)
H23	1.3170	0.9596	−0.1662	0.050*
C24	1.3917 (2)	0.78443 (18)	−0.09375 (15)	0.0365 (5)
H24	1.4348	0.7688	−0.1514	0.044*
C25	1.3406 (2)	0.71987 (19)	0.07506 (15)	0.0462 (5)
H25	1.3463	0.6586	0.1370	0.055*
C26	1.2703 (2)	0.8323 (2)	0.07211 (17)	0.0516 (6)
H26	1.2310	0.8454	0.1316	0.062*
C27	0.64387 (19)	1.11445 (16)	0.41277 (14)	0.0309 (4)
C28	0.4906 (2)	1.1779 (2)	0.44208 (17)	0.0562 (6)
H28B	0.4395	1.2429	0.3804	0.067*
H28A	0.4351	1.1245	0.4604	0.067*
C29	0.47920 (19)	1.22539 (19)	0.52763 (16)	0.0391 (5)
C30	0.5024 (2)	1.1515 (2)	0.62991 (18)	0.0489 (6)
H30	0.5273	1.0713	0.6462	0.059*
C31	0.4885 (2)	1.1967 (3)	0.70858 (19)	0.0643 (7)
H31	0.5078	1.1462	0.7772	0.077*
C32	0.4469 (3)	1.3141 (3)	0.6860 (3)	0.0713 (9)
H32	0.4356	1.3440	0.7390	0.086*
C33	0.4220 (3)	1.3873 (3)	0.5859 (3)	0.0703 (8)
H33	0.3929	1.4677	0.5704	0.084*
C34	0.4393 (2)	1.3440 (2)	0.50720 (19)	0.0544 (6)
H34	0.4239	1.3955	0.4389	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0254 (2)	0.0287 (2)	0.0267 (2)	−0.00973 (17)	0.00331 (16)	−0.01524 (19)
Mn2	0.0266 (2)	0.0352 (2)	0.0289 (2)	−0.01084 (18)	0.00248 (17)	−0.0132 (2)
Cl	0.0320 (3)	0.0543 (3)	0.0350 (3)	−0.0170 (2)	0.0077 (2)	−0.0155 (3)
O1	0.0243 (6)	0.0468 (9)	0.0401 (8)	−0.0071 (6)	−0.0008 (6)	−0.0228 (7)
O2	0.0481 (8)	0.0678 (11)	0.0427 (9)	−0.0074 (8)	−0.0051 (7)	−0.0328 (9)
N1	0.0308 (8)	0.0281 (9)	0.0316 (9)	−0.0120 (7)	0.0024 (7)	−0.0137 (8)
N2	0.0319 (8)	0.0328 (9)	0.0306 (9)	−0.0118 (7)	0.0016 (7)	−0.0126 (8)
N3	0.0316 (8)	0.0299 (9)	0.0323 (9)	−0.0111 (7)	0.0041 (7)	−0.0157 (8)
N4	0.0369 (9)	0.0394 (10)	0.0313 (9)	−0.0116 (8)	0.0017 (7)	−0.0162 (9)
C1	0.0298 (10)	0.0485 (13)	0.0595 (14)	−0.0130 (10)	0.0121 (10)	−0.0356 (12)
C2	0.0279 (10)	0.0485 (13)	0.0573 (13)	−0.0175 (10)	0.0071 (9)	−0.0326 (12)
C3	0.0276 (10)	0.0374 (12)	0.0560 (13)	−0.0078 (9)	0.0054 (9)	−0.0272 (11)
C4	0.0290 (10)	0.0444 (13)	0.0621 (14)	−0.0134 (9)	−0.0010 (9)	−0.0313 (12)
C5	0.0374 (10)	0.0305 (11)	0.0317 (10)	−0.0139 (9)	0.0035 (8)	−0.0156 (9)
C6	0.0477 (12)	0.0397 (12)	0.0384 (12)	−0.0200 (10)	0.0090 (9)	−0.0237 (11)
C7	0.0343 (10)	0.0407 (12)	0.0330 (11)	−0.0143 (9)	0.0011 (8)	−0.0205 (10)
C8	0.0366 (10)	0.0281 (11)	0.0325 (10)	−0.0093 (9)	−0.0032 (8)	−0.0119 (9)
C9	0.0333 (10)	0.0217 (10)	0.0327 (11)	−0.0074 (8)	−0.0003 (8)	−0.0146 (9)
C10	0.0369 (11)	0.0421 (12)	0.0340 (11)	−0.0220 (10)	0.0049 (9)	−0.0153 (10)
C11	0.0419 (11)	0.0412 (12)	0.0268 (10)	−0.0196 (10)	0.0027 (9)	−0.0101 (10)
C12	0.0340 (11)	0.0458 (13)	0.0376 (12)	−0.0199 (10)	0.0063 (9)	−0.0138 (11)
C13	0.0422 (11)	0.0447 (13)	0.0263 (10)	−0.0192 (10)	0.0035 (9)	−0.0118 (10)
C14	0.0438 (12)	0.0343 (11)	0.0313 (11)	−0.0092 (9)	0.0007 (9)	−0.0144 (10)
C15	0.0292 (10)	0.0374 (12)	0.0375 (12)	−0.0110 (9)	0.0036 (9)	−0.0168 (10)
C16	0.0346 (10)	0.0369 (12)	0.0409 (12)	−0.0142 (9)	0.0028 (9)	−0.0191 (10)
C17	0.0376 (11)	0.0361 (12)	0.0499 (13)	−0.0185 (10)	0.0108 (10)	−0.0182 (11)
C18	0.0480 (12)	0.0213 (10)	0.0385 (11)	−0.0126 (9)	0.0128 (10)	−0.0141 (10)
C19	0.0703 (15)	0.0333 (12)	0.0449 (13)	−0.0235 (11)	0.0222 (11)	−0.0144 (11)
C20	0.0639 (14)	0.0472 (14)	0.0469 (13)	−0.0228 (12)	0.0251 (11)	−0.0234 (12)
C21	0.0581 (14)	0.0504 (15)	0.0564 (15)	−0.0063 (12)	0.0010 (11)	−0.0305 (13)
C22	0.0422 (11)	0.0436 (13)	0.0434 (13)	−0.0093 (10)	0.0005 (10)	−0.0253 (12)
C23	0.0496 (12)	0.0405 (13)	0.0356 (11)	−0.0136 (10)	0.0021 (9)	−0.0160 (11)
C24	0.0412 (11)	0.0404 (12)	0.0309 (11)	−0.0135 (10)	0.0042 (9)	−0.0170 (11)
C25	0.0618 (14)	0.0475 (14)	0.0290 (11)	−0.0181 (11)	0.0048 (10)	−0.0142 (11)
C26	0.0678 (15)	0.0540 (15)	0.0366 (13)	−0.0148 (12)	0.0114 (11)	−0.0276 (13)
C27	0.0320 (10)	0.0283 (11)	0.0331 (11)	−0.0114 (8)	0.0018 (9)	−0.0107 (9)
C28	0.0266 (11)	0.0852 (18)	0.0659 (15)	−0.0084 (11)	0.0010 (10)	−0.0474 (15)
C29	0.0187 (9)	0.0516 (14)	0.0517 (14)	−0.0080 (9)	0.0041 (9)	−0.0280 (12)
C30	0.0305 (11)	0.0498 (14)	0.0603 (15)	−0.0047 (10)	0.0035 (10)	−0.0213 (13)
C31	0.0351 (12)	0.100 (2)	0.0500 (14)	−0.0094 (14)	0.0028 (11)	−0.0306 (16)
C32	0.0425 (14)	0.112 (3)	0.094 (2)	−0.0270 (16)	0.0149 (14)	−0.078 (2)
C33	0.0529 (15)	0.0646 (19)	0.119 (3)	−0.0260 (14)	0.0207 (16)	−0.059 (2)
C34	0.0408 (12)	0.0527 (15)	0.0654 (16)	−0.0159 (11)	0.0111 (11)	−0.0176 (14)

Geometric parameters (Å, º) top

Mn1—O1	2.1925 (11)	C11—H11	0.9300
Mn1—O1ⁱ	2.1925 (11)	C12—C13	1.380 (2)
Mn1—N3ⁱ	2.2891 (15)	C12—H12	0.9300
Mn1—N3	2.2891 (15)	C13—H13	0.9300
Mn1—N1	2.3504 (12)	C14—C15	1.380 (3)
Mn1—N1ⁱ	2.3505 (12)	C14—C18	1.382 (3)
Mn2—N4ⁱⁱ	2.3374 (15)	C14—H14	0.9300
Mn2—N4ⁱⁱⁱ	2.3374 (15)	C15—H15	0.9300
Mn2—N2	2.3425 (14)	C16—C17	1.376 (3)
Mn2—N2^iv	2.3425 (14)	C16—H16	0.9300
Mn2—Cl^iv	2.5081 (5)	C17—C18	1.381 (3)
Mn2—Cl	2.5081 (5)	C17—H17	0.9300
O1—C27	1.263 (2)	C18—C19	1.508 (3)
O2—C27	1.2309 (19)	C19—C20	1.545 (3)
N1—C3	1.330 (2)	C19—H19B	0.9700
N1—C2	1.338 (2)	C19—H19A	0.9700
N2—C12	1.337 (2)	C20—C21	1.522 (3)
N2—C11	1.340 (2)	C20—H20B	0.9700
N3—C16	1.334 (2)	C20—H20A	0.9700
N3—C15	1.341 (2)	C21—C22	1.506 (3)
N4—C24	1.333 (2)	C21—H21A	0.9700
N4—C25	1.339 (2)	C21—H21B	0.9700
N4—Mn2^v	2.3374 (15)	C22—C26	1.382 (3)
C1—C2	1.374 (2)	C22—C23	1.391 (2)
C1—C5	1.378 (2)	C23—C24	1.380 (3)
C1—H1	0.9300	C23—H23	0.9300
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.384 (2)	C25—C26	1.371 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.371 (2)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.524 (3)
C5—C6	1.507 (2)	C28—C29	1.501 (2)
C6—C7	1.518 (3)	C28—H28B	0.9700
C6—H6B	0.9700	C28—H28A	0.9700
C6—H6A	0.9700	C29—C30	1.381 (3)
C7—C8	1.532 (2)	C29—C34	1.381 (3)
C7—H7A	0.9700	C30—C31	1.391 (3)
C7—H7B	0.9700	C30—H30	0.9300
C8—C9	1.504 (2)	C31—C32	1.360 (4)
C8—H8B	0.9700	C31—H31	0.9300
C8—H8A	0.9700	C32—C33	1.354 (4)
C9—C10	1.379 (2)	C32—H32	0.9300
C9—C13	1.385 (2)	C33—C34	1.372 (3)
C10—C11	1.376 (2)	C33—H33	0.9300
C10—H10	0.9300	C34—H34	0.9300

O1—Mn1—O1ⁱ	180.00 (8)	N2—C11—H11	118.0
O1—Mn1—N3ⁱ	86.18 (5)	C10—C11—H11	118.0
O1ⁱ—Mn1—N3ⁱ	93.82 (5)	N2—C12—C13	123.72 (16)
O1—Mn1—N3	93.82 (5)	N2—C12—H12	118.1
O1ⁱ—Mn1—N3	86.18 (5)	C13—C12—H12	118.1
N3ⁱ—Mn1—N3	180.00 (7)	C12—C13—C9	120.04 (17)
O1—Mn1—N1	94.53 (4)	C12—C13—H13	120.0
O1ⁱ—Mn1—N1	85.47 (4)	C9—C13—H13	120.0
N3ⁱ—Mn1—N1	95.63 (5)	C15—C14—C18	120.39 (17)
N3—Mn1—N1	84.37 (5)	C15—C14—H14	119.8
O1—Mn1—N1ⁱ	85.47 (4)	C18—C14—H14	119.8
O1ⁱ—Mn1—N1ⁱ	94.53 (4)	N3—C15—C14	122.83 (16)
N3ⁱ—Mn1—N1ⁱ	84.37 (5)	N3—C15—H15	118.6
N3—Mn1—N1ⁱ	95.63 (5)	C14—C15—H15	118.6
N1—Mn1—N1ⁱ	179.999 (2)	N3—C16—C17	124.04 (17)
N4ⁱⁱ—Mn2—N4ⁱⁱⁱ	180.0	N3—C16—H16	118.0
N4ⁱⁱ—Mn2—N2	89.48 (5)	C17—C16—H16	118.0
N4ⁱⁱⁱ—Mn2—N2	90.52 (5)	C16—C17—C18	119.62 (16)
N4ⁱⁱ—Mn2—N2^iv	90.52 (5)	C16—C17—H17	120.2
N4ⁱⁱⁱ—Mn2—N2^iv	89.48 (5)	C18—C17—H17	120.2
N2—Mn2—N2^iv	180.0	C17—C18—C14	116.66 (17)
N4ⁱⁱ—Mn2—Cl^iv	90.26 (4)	C17—C18—C19	120.68 (17)
N4ⁱⁱⁱ—Mn2—Cl^iv	89.74 (4)	C14—C18—C19	122.58 (18)
N2—Mn2—Cl^iv	91.14 (4)	C18—C19—C20	111.16 (17)
N2^iv—Mn2—Cl^iv	88.86 (4)	C18—C19—H19B	109.4
N4ⁱⁱ—Mn2—Cl	89.74 (4)	C20—C19—H19B	109.4
N4ⁱⁱⁱ—Mn2—Cl	90.26 (4)	C18—C19—H19A	109.4
N2—Mn2—Cl	88.86 (4)	C20—C19—H19A	109.4
N2^iv—Mn2—Cl	91.14 (4)	H19B—C19—H19A	108.0
Cl^iv—Mn2—Cl	180.0	C21—C20—C19	112.69 (18)
C27—O1—Mn1	146.73 (11)	C21—C20—H20B	109.1
C3—N1—C2	115.84 (14)	C19—C20—H20B	109.1
C3—N1—Mn1	123.51 (11)	C21—C20—H20A	109.1
C2—N1—Mn1	120.59 (10)	C19—C20—H20A	109.1
C12—N2—C11	115.74 (15)	H20B—C20—H20A	107.8
C12—N2—Mn2	124.04 (11)	C22—C21—C20	113.31 (18)
C11—N2—Mn2	120.22 (12)	C22—C21—H21A	108.9
C16—N3—C15	116.38 (15)	C20—C21—H21A	108.9
C16—N3—Mn1	121.77 (12)	C22—C21—H21B	108.9
C15—N3—Mn1	121.06 (11)	C20—C21—H21B	108.9
C24—N4—C25	116.24 (17)	H21A—C21—H21B	107.7
C24—N4—Mn2^v	122.37 (11)	C26—C22—C23	116.10 (19)
C25—N4—Mn2^v	121.18 (14)	C26—C22—C21	120.97 (17)
C2—C1—C5	120.49 (17)	C23—C22—C21	122.9 (2)
C2—C1—H1	119.8	C24—C23—C22	119.6 (2)
C5—C1—H1	119.8	C24—C23—H23	120.2
N1—C2—C1	123.68 (16)	C22—C23—H23	120.2
N1—C2—H2	118.2	N4—C24—C23	124.00 (17)
C1—C2—H2	118.2	N4—C24—H24	118.0
N1—C3—C4	123.36 (16)	C23—C24—H24	118.0
N1—C3—H3	118.3	N4—C25—C26	123.3 (2)
C4—C3—H3	118.3	N4—C25—H25	118.4
C5—C4—C3	120.74 (16)	C26—C25—H25	118.4
C5—C4—H4	119.6	C25—C26—C22	120.80 (18)
C3—C4—H4	119.6	C25—C26—H26	119.6
C4—C5—C1	115.90 (15)	C22—C26—H26	119.6
C4—C5—C6	121.64 (15)	O2—C27—O1	125.80 (17)
C1—C5—C6	122.42 (16)	O2—C27—C28	114.92 (16)
C5—C6—C7	111.65 (14)	O1—C27—C28	119.24 (15)
C5—C6—H6B	109.3	C29—C28—C27	119.64 (15)
C7—C6—H6B	109.3	C29—C28—H28B	107.4
C5—C6—H6A	109.3	C27—C28—H28B	107.4
C7—C6—H6A	109.3	C29—C28—H28A	107.4
H6B—C6—H6A	108.0	C27—C28—H28A	107.4
C6—C7—C8	114.66 (14)	H28B—C28—H28A	106.9
C6—C7—H7A	108.6	C30—C29—C34	117.88 (19)
C8—C7—H7A	108.6	C30—C29—C28	120.6 (2)
C6—C7—H7B	108.6	C34—C29—C28	121.4 (2)
C8—C7—H7B	108.6	C29—C30—C31	120.1 (2)
H7A—C7—H7B	107.6	C29—C30—H30	119.9
C9—C8—C7	113.34 (15)	C31—C30—H30	119.9
C9—C8—H8B	108.9	C32—C31—C30	120.6 (3)
C7—C8—H8B	108.9	C32—C31—H31	119.7
C9—C8—H8A	108.9	C30—C31—H31	119.7
C7—C8—H8A	108.9	C33—C32—C31	119.6 (2)
H8B—C8—H8A	107.7	C33—C32—H32	120.2
C10—C9—C13	116.48 (16)	C31—C32—H32	120.2
C10—C9—C8	121.62 (15)	C32—C33—C34	120.6 (2)
C13—C9—C8	121.89 (16)	C32—C33—H33	119.7
C11—C10—C9	120.01 (16)	C34—C33—H33	119.7
C11—C10—H10	120.0	C33—C34—C29	121.1 (2)
C9—C10—H10	120.0	C33—C34—H34	119.4
N2—C11—C10	124.01 (17)	C29—C34—H34	119.4

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

Experimental details

Crystal data
Chemical formula	[Mn₂(C₈H₇O₂)₂Cl₂(C₁₃H₁₄N₂)₄]
M_r	1244.10
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5594 (5), 13.0091 (6), 13.8484 (6)
α, β, γ (°)	69.202 (4), 86.318 (4), 69.910 (5)
V (Å³)	1508.74 (13)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.48 × 0.46 × 0.23

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.77, 0.88
No. of measured, independent and observed [I > 2σ(I)] reflections	10180, 5303, 4041
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.069, 0.96
No. of reflections	5303
No. of parameters	383
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This project was supported by the Expert Project of Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), the Science and Technology Department of Zhejiang Province (grant No. 2006 C21105), and the Education Department of Zhejiang Province. Thanks are also extended the to K. C. Wong Magna Fund in Ningbo University.

References

Biradha, K., Sarkar, M. & Rajput, L. (2006). Chem. Commun. pp. 4169–4179. Web of Science CrossRef Google Scholar
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Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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