Poly[(μ4-biphenyl-3,3′-dicarboxyl­ato)bis[μ2-1,1′-(butane-1,4-di­yl)diimidazole](μ2-oxalato)dimanganese(II)]

Zhu, B.-Y.

doi:10.1107/S1600536810035269

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1214

doi:10.1107/S1600536810035269

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Poly[(μ₄-biphenyl-3,3′-dicarboxylato)bis[μ₂-1,1′-(butane-1,4-diyl)diimidazole](μ₂-oxalato)dimanganese(II)]

Bao-Yong Zhu ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: zhubaoyong@yahoo.cn

(Received 21 August 2010; accepted 1 September 2010; online 4 September 2010)

In the title coordination compound, [Mn₂(C₁₄H₈O₄)(C₂O₄)(C₁₀H₁₄N₄)₂]_n, the biphenyl-3,3′-dicarboxylate and oxalate anions, both situated on inversion centres, function in a bridging mode, linking the dinuclear Mn^II atoms into wave-like layers. Each 1,1′-(1,4-butane-1,4-diyl)diimidazole ligand coordinates to two Mn^II atoms located in adjacent layers via Mn—N coordination bonds, giving a three-dimensional network. As the methylene groups can bend freely relative to each other due to the C atoms connected via single bonds, the 1,1′-(butane-1,4-diyl)diimidazole ligand forms an S-shaped conformation, which makes the void in the three-dimensional network distorted.

Related literature

For the synthesis of the ligand, see: Yang et al. (2005 ). For the structures of related complexes, see: Wang et al. (2005 ). For related structures, see: Zhang et al. (2008 ); Zhou et al. (2009 ).

Experimental

Crystal data

[Mn₂(C₁₄H₈O₄)(C₂O₄)(C₁₀H₁₄N₄)₂]
M_r = 818.60
Triclinic, $[P \overline 1]$
a = 9.532 (8) Å
b = 9.881 (8) Å
c = 11.051 (9) Å
α = 104.397 (2)°
β = 99.707 (2)°
γ = 114.265 (5)°
V = 874.8 (12) Å³
Z = 1
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 296 K
0.13 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.902, T_max = 0.923
4577 measured reflections
3063 independent reflections
2495 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.01
3063 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT ; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035269/hg2706sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035269/hg2706Isup2.hkl

checkCIF report

Comment top

Single crystal X-ray crystallographic analysis reveals that (I) crystallizes in triclinic system, space group P-1. It consists of dinuclear units of Mn^II atoms and the separation between the dinuclear Mn^II atoms is 4.823 (2) Å. The coordination environment around each Mn^II atom is shown in Figure 1 with the atom numbering scheme. In the asymmetric unit, there is one Mn^II atom, one 1,1'-(butane-1,4-diyl)diimidazole (bbi) ligand, half a 3, 3'-biphenyldicarboxylate (3, 3'-bpda) ligand and half an oxalate (ox) anion. The Mn^II atom is six-coordinated with distorted octahedral coordination geometry by two nitrogen (N1ⁱ, N4) atoms of two distinct bbi ligands with Mn - N bond lengths of 2.257 (5) and 2.261 (6) Å and four oxygen atoms (O1ⁱⁱ, O2, O3, O4ⁱⁱⁱ) from two distinct 3, 3'-bpda ligands and one ox ligand with Mn-O bond lengths in the range of 2.234 (4)-2.155 (4) Å, and the coordination angles around Mn1 are in the range of 85.7 (2) to 178.2 (2) ° (Table 1). The ox anion coordinates to two Mn^II centers via a chelating bis-bidentate coordination mode and serves as a bridging ligand. 3, 3'-bpda ligand adopts a trans conformation and acts as a bis-bidentate bridging ligand, the carboxylate groups are slightly twisted with respect to correspondingly linking phenyl rings with the dihedral angles 6.5 and 9.5°. The dihedral angle between two phenyl rings about the central bond is 0 °, which suggests the two phenyl rings are coplanar, showing a perfect trans conformation, which is different from that observed in metal-organic complexes reported previously (Wang et al., 2005). The Mn^II atoms are linked by 3, 3'-bpda and ox ligands into wave-like two dimensional layers (Fig. 2). Each bbi ligand coordinates to two Mn^II centers located in adjacent layers via Mn-N coordination bonds to give rise to a three-dimensional network (Fig. 3).

It is noteworthy that the flexibility of the bbi ligand has a great influence to the framework. In structure of (I), because the methylene can bend freely to each other, the bbi ligand form a "S" shape conformation, which makes the void in the three-dimensional network distorted. This may reduce the surface energy of the framework and result in the uninterpenetrating three-dimensional framework of (I), unlike previously reported relate structures (Zhang et al., 2008; Zhou et al., 2009), which are composed of equivalent mutually interpenetrating networks. The distance between two Mn^II centers linked by bbi ligand is 12.87 Å, shorter than previously reported relevant structure (Zhang et al., 2008).

Related literature top

For the synthesis of the ligand, see: Yang et al. (2005). For the conformation of related complexes, see: Wang et al. (2005). For related structures, see: Zhang et al. (2008); Zhou et al. (2009).

Experimental top

The ligand bbi was synthesized according to the literature (Yang et al., 2005). For the synthesis of (I), a mixture of 3, 3'-bpda (0.024 g, 0.1 mmol), bbi (0.021 g, 0.1 mmol), MnCl₂4H₂O (0.020 g, 0.1 mmol), and NaOH (0.008 g, 0.2 mmol) in H₂O (7.0 ml) was placed in a 16 ml Teflon-lined stainless steel vessel and heated to 180 °C for 72 h to give rise to colorless block crystals of (I), which were collected by filtration. The colorless crystals obtained were washed with water and dried in air. Yield: 0.046 g (56% based on 3, 3'-bpda). IR (KBr pellet, cm^-1): 3422(w), 3123(w), 1642(s), 1604(s), 1563(s), 1517(m), 1469(w), 1447(w), 1380(s), 1310(s), 1278(m), 1233(s), 1107(s), 1094(s), 936(s), 826(s), 782(s), 682(m), 657(s), 497(m).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL(Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the MnII coordination environment of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. Symmetry code: (i) x, -1 + y, -1 + z; (ii) 2-x, 1-y, -z; (iii) 1-x, -y, -z; (iv) -x, -1 - y, -1-z.
	Fig. 2. Perspective view of the two-dimensional layer of (I).
	Fig. 3. View of a three- dimensional framework of (I).

Poly[(µ₄-biphenyl-3,3'-dicarboxylato)bis[µ₂-1,1'-(butane-1,4- diyl)diimidazole](µ₂-oxalato)dimanganese(II)] top

Crystal data top

[Mn₂(C₁₄H₈O₄)(C₂O₄)(C₁₀H₁₄N₄)₂]	Z = 1
M_r = 818.60	F(000) = 422
Triclinic, P1	D_x = 1.554 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.532 (8) Å	Cell parameters from 1712 reflections
b = 9.881 (8) Å	θ = 2.5–27.1°
c = 11.051 (9) Å	µ = 0.79 mm⁻¹
α = 104.397 (2)°	T = 296 K
β = 99.707 (2)°	Block, colorless
γ = 114.265 (5)°	0.13 × 0.11 × 0.10 mm
V = 874.8 (12) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3063 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→11
T_min = 0.902, T_max = 0.923	k = −11→11
4577 measured reflections	l = −13→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0337P)² + 0.7805P] where P = (F_o² + 2F_c²)/3
3063 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Mn₂(C₁₄H₈O₄)(C₂O₄)(C₁₀H₁₄N₄)₂]	γ = 114.265 (5)°
M_r = 818.60	V = 874.8 (12) Å³
Triclinic, P1	Z = 1
a = 9.532 (8) Å	Mo Kα radiation
b = 9.881 (8) Å	µ = 0.79 mm⁻¹
c = 11.051 (9) Å	T = 296 K
α = 104.397 (2)°	0.13 × 0.11 × 0.10 mm
β = 99.707 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3063 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2495 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.923	R_int = 0.020
4577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.01	Δρ_max = 0.71 e Å⁻³
3063 reflections	Δρ_min = −0.36 e Å⁻³
244 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.7299 (4)	0.9282 (4)	0.7716 (3)	0.0427 (8)
H1	0.6181	0.8815	0.7375	0.051*
C2	0.9736 (4)	1.0911 (5)	0.8827 (4)	0.0633 (11)
H2	1.0655	1.1814	0.9418	0.076*
C3	0.9734 (5)	0.9615 (5)	0.8048 (4)	0.0713 (12)
H3	1.0628	0.9464	0.8006	0.086*
C4	0.7560 (5)	0.6974 (4)	0.6402 (3)	0.0564 (10)
H4A	0.6452	0.6333	0.6363	0.068*
H4B	0.8193	0.6507	0.6722	0.068*
C5	0.7612 (6)	0.6915 (5)	0.5041 (4)	0.0768 (13)
H5A	0.8727	0.7552	0.5093	0.092*
H5B	0.7285	0.5827	0.4517	0.092*
C6	0.6637 (6)	0.7444 (5)	0.4343 (4)	0.0816 (14)
H6A	0.6957	0.8530	0.4863	0.098*
H6B	0.5517	0.6801	0.4278	0.098*
C7	0.6733 (6)	0.7376 (4)	0.2962 (4)	0.0642 (11)
H7A	0.6072	0.7796	0.2600	0.077*
H7B	0.7841	0.8044	0.3016	0.077*
C8	0.4624 (4)	0.4587 (4)	0.1455 (3)	0.0505 (9)
H8	0.3691	0.4661	0.1502	0.061*
C9	0.4710 (4)	0.3296 (4)	0.0757 (3)	0.0444 (8)
H9	0.3825	0.2319	0.0237	0.053*
C10	0.7130 (4)	0.5128 (4)	0.1726 (3)	0.0423 (8)
H10	0.8254	0.5686	0.2016	0.051*
C11	1.0488 (3)	0.4969 (3)	0.0624 (2)	0.0253 (6)
C12	0.3716 (3)	−0.0489 (3)	−0.1928 (2)	0.0240 (6)
C13	0.2848 (3)	−0.1643 (3)	−0.3312 (2)	0.0262 (6)
C14	0.1514 (3)	−0.3102 (3)	−0.3588 (2)	0.0257 (6)
H14	0.1146	−0.3347	−0.2904	0.031*
C15	0.0709 (3)	−0.4210 (3)	−0.4862 (3)	0.0261 (6)
C16	0.1284 (3)	−0.3790 (3)	−0.5861 (3)	0.0344 (7)
H16	0.0772	−0.4505	−0.6720	0.041*
C17	0.2597 (4)	−0.2338 (3)	−0.5611 (3)	0.0408 (8)
H17	0.2949	−0.2082	−0.6298	0.049*
C18	0.3386 (4)	−0.1266 (3)	−0.4339 (3)	0.0352 (7)
H18	0.4276	−0.0293	−0.4169	0.042*
Mn1	0.72380 (5)	0.21542 (5)	−0.02078 (4)	0.02532 (14)
N1	0.8196 (3)	1.0703 (3)	0.8619 (2)	0.0365 (6)
N2	0.8173 (3)	0.8581 (3)	0.7341 (2)	0.0443 (7)
N3	0.6182 (4)	0.5751 (3)	0.2074 (2)	0.0451 (7)
N4	0.6292 (3)	0.3645 (3)	0.0931 (2)	0.0365 (6)
O1	1.1919 (2)	0.6036 (2)	0.11609 (18)	0.0324 (5)
O2	0.9760 (2)	0.3849 (2)	0.09977 (17)	0.0318 (5)
O3	0.5021 (2)	0.0710 (2)	−0.17499 (18)	0.0326 (5)
O4	0.3098 (2)	−0.0764 (2)	−0.10413 (17)	0.0310 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0386 (18)	0.0441 (18)	0.0401 (18)	0.0215 (16)	0.0121 (14)	0.0027 (15)
C2	0.039 (2)	0.064 (2)	0.066 (3)	0.0244 (19)	0.0084 (18)	−0.004 (2)
C3	0.053 (2)	0.078 (3)	0.079 (3)	0.043 (2)	0.017 (2)	0.001 (2)
C4	0.082 (3)	0.046 (2)	0.047 (2)	0.041 (2)	0.0196 (19)	0.0089 (16)
C5	0.126 (4)	0.066 (3)	0.044 (2)	0.062 (3)	0.018 (2)	0.0044 (19)
C6	0.136 (4)	0.067 (3)	0.052 (3)	0.071 (3)	0.018 (3)	0.004 (2)
C7	0.111 (3)	0.048 (2)	0.047 (2)	0.052 (2)	0.025 (2)	0.0127 (17)
C8	0.054 (2)	0.071 (2)	0.0406 (19)	0.042 (2)	0.0193 (17)	0.0181 (18)
C9	0.046 (2)	0.0482 (19)	0.0398 (18)	0.0234 (17)	0.0171 (15)	0.0127 (15)
C10	0.0470 (19)	0.0421 (18)	0.0361 (17)	0.0230 (16)	0.0115 (14)	0.0084 (14)
C11	0.0246 (14)	0.0209 (13)	0.0227 (14)	0.0074 (12)	0.0068 (11)	0.0017 (11)
C12	0.0223 (14)	0.0221 (13)	0.0213 (14)	0.0079 (12)	0.0028 (11)	0.0048 (11)
C13	0.0234 (14)	0.0239 (13)	0.0238 (14)	0.0082 (11)	0.0036 (11)	0.0044 (11)
C14	0.0272 (14)	0.0229 (13)	0.0194 (13)	0.0084 (12)	0.0040 (11)	0.0037 (10)
C15	0.0232 (14)	0.0218 (13)	0.0237 (14)	0.0064 (12)	0.0034 (11)	0.0032 (11)
C16	0.0364 (16)	0.0276 (15)	0.0199 (14)	0.0046 (13)	0.0030 (12)	0.0004 (12)
C17	0.0437 (18)	0.0343 (16)	0.0259 (16)	0.0031 (14)	0.0120 (13)	0.0076 (13)
C18	0.0347 (16)	0.0252 (15)	0.0270 (15)	0.0007 (13)	0.0084 (12)	0.0041 (12)
Mn1	0.0227 (2)	0.0210 (2)	0.0202 (2)	0.00355 (17)	0.00432 (16)	0.00186 (16)
N1	0.0367 (14)	0.0374 (14)	0.0309 (13)	0.0189 (12)	0.0091 (11)	0.0032 (11)
N2	0.0532 (17)	0.0477 (16)	0.0342 (15)	0.0306 (14)	0.0137 (13)	0.0059 (12)
N3	0.069 (2)	0.0442 (16)	0.0321 (14)	0.0374 (16)	0.0166 (14)	0.0108 (12)
N4	0.0448 (15)	0.0349 (14)	0.0277 (13)	0.0205 (12)	0.0116 (11)	0.0045 (11)
O1	0.0249 (10)	0.0301 (10)	0.0270 (10)	0.0030 (9)	0.0014 (8)	0.0082 (8)
O2	0.0292 (11)	0.0268 (10)	0.0242 (10)	0.0028 (9)	0.0028 (8)	0.0073 (8)
O3	0.0240 (10)	0.0249 (10)	0.0291 (10)	−0.0001 (9)	0.0022 (8)	0.0029 (8)
O4	0.0338 (11)	0.0268 (10)	0.0217 (10)	0.0076 (9)	0.0068 (8)	0.0047 (8)

Geometric parameters (Å, º) top

C1—N1	1.314 (4)	C10—H10	0.9300
C1—N2	1.339 (4)	C11—O1	1.248 (3)
C1—H1	0.9300	C11—O2	1.252 (3)
C2—C3	1.353 (5)	C11—C11ⁱ	1.559 (5)
C2—N1	1.366 (4)	C12—O4	1.256 (3)
C2—H2	0.9300	C12—O3	1.257 (3)
C3—N2	1.352 (5)	C12—C13	1.502 (3)
C3—H3	0.9300	C13—C18	1.392 (4)
C4—N2	1.467 (4)	C13—C14	1.390 (4)
C4—C5	1.501 (5)	C14—C15	1.396 (4)
C4—H4A	0.9700	C14—H14	0.9300
C4—H4B	0.9700	C15—C16	1.392 (4)
C5—C6	1.446 (6)	C15—C15ⁱⁱ	1.500 (5)
C5—H5A	0.9700	C16—C17	1.382 (4)
C5—H5B	0.9700	C16—H16	0.9300
C6—C7	1.532 (5)	C17—C18	1.383 (4)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—H18	0.9300
C7—N3	1.472 (4)	Mn1—O3	2.1222 (19)
C7—H7A	0.9700	Mn1—O4ⁱⁱⁱ	2.151 (2)
C7—H7B	0.9700	Mn1—O2	2.205 (2)
C8—C9	1.360 (5)	Mn1—O1ⁱ	2.235 (2)
C8—N3	1.364 (4)	Mn1—N4	2.263 (2)
C8—H8	0.9300	Mn1—N1^iv	2.263 (2)
C9—N4	1.368 (4)	N1—Mn1^v	2.263 (2)
C9—H9	0.9300	O1—Mn1ⁱ	2.235 (2)
C10—N4	1.311 (4)	O4—Mn1ⁱⁱⁱ	2.151 (2)
C10—N3	1.341 (4)

N1—C1—N2	112.6 (3)	C18—C13—C12	120.0 (2)
N1—C1—H1	123.7	C14—C13—C12	120.9 (2)
N2—C1—H1	123.7	C13—C14—C15	122.0 (2)
C3—C2—N1	110.2 (3)	C13—C14—H14	119.0
C3—C2—H2	124.9	C15—C14—H14	119.0
N1—C2—H2	124.9	C16—C15—C14	117.3 (2)
C2—C3—N2	106.4 (3)	C16—C15—C15ⁱⁱ	121.5 (3)
C2—C3—H3	126.8	C14—C15—C15ⁱⁱ	121.2 (3)
N2—C3—H3	126.8	C17—C16—C15	121.7 (2)
N2—C4—C5	114.0 (3)	C17—C16—H16	119.1
N2—C4—H4A	108.8	C15—C16—H16	119.1
C5—C4—H4A	108.8	C18—C17—C16	120.0 (3)
N2—C4—H4B	108.8	C18—C17—H17	120.0
C5—C4—H4B	108.8	C16—C17—H17	120.0
H4A—C4—H4B	107.7	C17—C18—C13	119.9 (3)
C6—C5—C4	117.6 (4)	C17—C18—H18	120.0
C6—C5—H5A	107.9	C13—C18—H18	120.0
C4—C5—H5A	107.9	O3—Mn1—O4ⁱⁱⁱ	99.95 (8)
C6—C5—H5B	107.9	O3—Mn1—O2	165.44 (7)
C4—C5—H5B	107.9	O4ⁱⁱⁱ—Mn1—O2	93.16 (7)
H5A—C5—H5B	107.2	O3—Mn1—O1ⁱ	92.32 (7)
C5—C6—C7	116.0 (4)	O4ⁱⁱⁱ—Mn1—O1ⁱ	167.71 (7)
C5—C6—H6A	108.3	O2—Mn1—O1ⁱ	74.74 (7)
C7—C6—H6A	108.3	O3—Mn1—N4	93.96 (9)
C5—C6—H6B	108.3	O4ⁱⁱⁱ—Mn1—N4	91.30 (9)
C7—C6—H6B	108.3	O2—Mn1—N4	92.05 (9)
H6A—C6—H6B	107.4	O1ⁱ—Mn1—N4	87.11 (9)
N3—C7—C6	112.3 (3)	O3—Mn1—N1^iv	85.82 (9)
N3—C7—H7A	109.1	O4ⁱⁱⁱ—Mn1—N1^iv	90.21 (9)
C6—C7—H7A	109.1	O2—Mn1—N1^iv	87.83 (9)
N3—C7—H7B	109.1	O1ⁱ—Mn1—N1^iv	91.42 (9)
C6—C7—H7B	109.1	N4—Mn1—N1^iv	178.50 (9)
H7A—C7—H7B	107.9	C1—N1—C2	104.3 (3)
C9—C8—N3	106.0 (3)	C1—N1—Mn1^v	125.1 (2)
C9—C8—H8	127.0	C2—N1—Mn1^v	129.6 (2)
N3—C8—H8	127.0	C1—N2—C3	106.6 (3)
C8—C9—N4	110.0 (3)	C1—N2—C4	127.0 (3)
C8—C9—H9	125.0	C3—N2—C4	126.4 (3)
N4—C9—H9	125.0	C10—N3—C8	106.7 (3)
N4—C10—N3	112.3 (3)	C10—N3—C7	126.2 (3)
N4—C10—H10	123.9	C8—N3—C7	127.0 (3)
N3—C10—H10	123.9	C10—N4—C9	105.0 (3)
O1—C11—O2	126.0 (2)	C10—N4—Mn1	127.0 (2)
O1—C11—C11ⁱ	117.2 (3)	C9—N4—Mn1	127.0 (2)
O2—C11—C11ⁱ	116.8 (3)	C11—O1—Mn1ⁱ	115.06 (17)
O4—C12—O3	124.7 (2)	C11—O2—Mn1	116.18 (16)
O4—C12—C13	118.9 (2)	C12—O3—Mn1	135.35 (17)
O3—C12—C13	116.5 (2)	C12—O4—Mn1ⁱⁱⁱ	143.26 (18)
C18—C13—C14	119.1 (2)

N1—C2—C3—N2	0.1 (5)	C6—C7—N3—C10	−101.2 (4)
N2—C4—C5—C6	−63.2 (5)	C6—C7—N3—C8	78.4 (5)
C4—C5—C6—C7	179.6 (4)	N3—C10—N4—C9	0.1 (4)
C5—C6—C7—N3	61.2 (6)	N3—C10—N4—Mn1	169.41 (19)
N3—C8—C9—N4	−0.2 (4)	C8—C9—N4—C10	0.0 (4)
O4—C12—C13—C18	171.3 (3)	C8—C9—N4—Mn1	−169.3 (2)
O3—C12—C13—C18	−7.9 (4)	O3—Mn1—N4—C10	−151.4 (3)
O4—C12—C13—C14	−9.4 (4)	O4ⁱⁱⁱ—Mn1—N4—C10	108.5 (3)
O3—C12—C13—C14	171.5 (2)	O2—Mn1—N4—C10	15.3 (3)
C18—C13—C14—C15	0.9 (4)	O1ⁱ—Mn1—N4—C10	−59.3 (3)
C12—C13—C14—C15	−178.5 (2)	O3—Mn1—N4—C9	15.6 (3)
C13—C14—C15—C16	−0.8 (4)	O4ⁱⁱⁱ—Mn1—N4—C9	−84.5 (2)
C13—C14—C15—C15ⁱⁱ	178.8 (3)	O2—Mn1—N4—C9	−177.7 (2)
C14—C15—C16—C17	0.0 (4)	O1ⁱ—Mn1—N4—C9	107.7 (2)
C15ⁱⁱ—C15—C16—C17	−179.6 (3)	O2—C11—O1—Mn1ⁱ	−179.1 (2)
C15—C16—C17—C18	0.7 (5)	C11ⁱ—C11—O1—Mn1ⁱ	0.8 (4)
C16—C17—C18—C13	−0.6 (5)	O1—C11—O2—Mn1	−179.2 (2)
C14—C13—C18—C17	−0.2 (4)	C11ⁱ—C11—O2—Mn1	0.9 (4)
C12—C13—C18—C17	179.2 (3)	O3—Mn1—O2—C11	26.9 (4)
N2—C1—N1—C2	0.0 (4)	O4ⁱⁱⁱ—Mn1—O2—C11	−178.85 (18)
N2—C1—N1—Mn1^v	−169.0 (2)	O1ⁱ—Mn1—O2—C11	−1.00 (17)
C3—C2—N1—C1	−0.1 (5)	N4—Mn1—O2—C11	−87.44 (19)
C3—C2—N1—Mn1^v	168.3 (3)	N1^iv—Mn1—O2—C11	91.06 (19)
N1—C1—N2—C3	0.0 (4)	O4—C12—O3—Mn1	33.5 (4)
N1—C1—N2—C4	177.0 (3)	C13—C12—O3—Mn1	−147.35 (19)
C2—C3—N2—C1	−0.1 (5)	O4ⁱⁱⁱ—Mn1—O3—C12	9.5 (3)
C2—C3—N2—C4	−177.1 (3)	O2—Mn1—O3—C12	163.4 (3)
C5—C4—N2—C1	97.7 (4)	O1ⁱ—Mn1—O3—C12	−169.7 (2)
C5—C4—N2—C3	−85.9 (5)	N4—Mn1—O3—C12	−82.5 (3)
N4—C10—N3—C8	−0.2 (4)	N1^iv—Mn1—O3—C12	99.0 (3)
N4—C10—N3—C7	179.4 (3)	O3—C12—O4—Mn1ⁱⁱⁱ	−102.2 (3)
C9—C8—N3—C10	0.2 (4)	C13—C12—O4—Mn1ⁱⁱⁱ	78.7 (3)
C9—C8—N3—C7	−179.4 (3)

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

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₄H₈O₄)(C₂O₄)(C₁₀H₁₄N₄)₂]
M_r	818.60
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.532 (8), 9.881 (8), 11.051 (9)
α, β, γ (°)	104.397 (2), 99.707 (2), 114.265 (5)
V (Å³)	874.8 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.13 × 0.11 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.902, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	4577, 3063, 2495
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.01
No. of reflections	3063
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL(Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

The author gratefully acknowledges the fund of Dezhou University.

References

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