Poly[(μ6-benzene-1,2,4,5-tetra­carboxyl­ato)bis­(1,10-phenanthroline-κ2N,N′)dimanganese(II)]

Jiang, X.-D.; Li, X.-B.; Sun, B.-W.

doi:10.1107/S1600536808016723

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m922-m923

doi:10.1107/S1600536808016723

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Poly[(μ₆-benzene-1,2,4,5-tetracarboxylato)bis(1,10-phenanthroline-κ²N,N′)dimanganese(II)]

Xin-Dong Jiang,^a Xiu-Bing Li ^b and Bai-Wang Sun ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 11 January 2008; accepted 2 June 2008; online 13 June 2008)

The title polymeric compound, [Mn₂(C₁₀H₂O₈)(C₁₂H₈N₂)₂]_n, was obtained by the reaction of manganese(II) chloride tetrahydrate with benzene-1,2,4,5-tetracarboxylic acid (H₄bta) in aqueous solution. Each Mn²⁺ ion is coordinated in a distorted octahedral geometry by two N atoms from one 1,10-phenanthroline ligand and four O atoms [Mn—O = 2.116 (2)–2.237 (2) Å] from three bta⁴⁻ ligands, which also act as bridging groups between the Mn²⁺ ions.

Related literature

For general background, see: Rao et al. (2000 ). For related structures, see: Aghabozorg et al. (2007 ); Chu et al. (2001 ); Liu & Ding (2007 ); Wu et al., (2006 ).

Experimental

Crystal data

[Mn₂(C₁₀H₂O₈)(C₁₂H₈N₂)₂]
M_r = 360.20
Monoclinic, P 2₁ /c
a = 7.5115 (7) Å
b = 19.8111 (19) Å
c = 9.6327 (9) Å
β = 112.027 (2)°
V = 1328.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Scxmini CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.796, T_max = 0.833
8026 measured reflections
2336 independent reflections
1853 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.107
S = 0.99
2336 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O2	2.116 (2)
Mn1—O3	2.125 (2)
Mn1—O4	2.204 (2)
Mn1—O1	2.237 (2)
Mn1—N2	2.252 (3)
Mn1—N1	2.305 (3)

O2—Mn1—O3	107.56 (9)
O2—Mn1—O4	81.59 (9)
O3—Mn1—O4	99.15 (8)
O2—Mn1—O1	96.86 (9)
O3—Mn1—O1	80.40 (8)
O4—Mn1—O1	178.19 (9)
O2—Mn1—N2	86.52 (9)
O3—Mn1—N2	156.89 (9)
O4—Mn1—N2	101.02 (9)
O1—Mn1—N2	79.78 (9)
O3—Mn1—N1	98.36 (9)
O4—Mn1—N1	85.10 (9)
O1—Mn1—N1	96.70 (9)
N2—Mn1—N1	72.38 (9)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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, New_Global_Publ_Block. DOI: 10.1107/S1600536808016723/rt2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016723/rt2017Isup2.hkl

checkCIF report

Comment top

The recent interest in the crystal engineering of special geometrical and topological coordination polymers arises from their potential application in catalysis, chemical absorption, magnetism and electrical conductivity (For related structures, see: Rao et al., 2000). The benzene-1,2,4,5-teracarboxylate ligand (bta) as a multi-connecting ligand is also an excellent candidate for the structuring of coordination polymers, and comparatively few examples have been reported to date in relation to applying it to the building of coordination polymers (For details of the preparation of related compounds, see: Aghabozorg et al., 2007; Chu et al., 2001; Liu & Ding, 2007; Wu et al., 2006). We report here the synthesis and crystal structure of the title complex, (I) (Fig. 1).

As shown in Fig.1, only one bta ligand is located in the crystallographic asymmetric unit, while each bta ligand is shared between three manganese(II) centres. The manganese atom is situated on an inversion centre and is coordinated in a trans mode by one chelated phen ligand [Mn—N = 2.252 (3) and 2.305 (3) Å] and four carboxylate oxygen atoms [Mn—O = 2.116 (2), 2.125 (2), 2.204 (2) and 2.237 (2) Å] (Table 1) from three distinct bta ligands. The coordination geometry around the Mn^II ion is slightly distorted octahedral. The O1 and O4 atoms occupy trans positions. Each bta ligand bridges to six manganese atoms to generate a two-dimensional sheet architecture, in which the carboxylate groups of the bta ligand all display a bridging mode (Fig. 2). Along the crystallographic a-axis, the manganese atoms are maintained in a pseudo-chain arrangement with a Mn···Mn distance of 4.611 Å (Fig. 3).

Related literature top

For general background, see: Rao et al. (2000). For related structures, see: Aghabozorg et al. (2007); Chu et al. (2001); Liu & Ding (2007); Wu et al., (2006). Scheme should reflect formula unit, with 2 Mn, 2 phen ligands, and 1 bta ligand with appropriate dangling bonds extending beyond the square brackets.

Experimental top

All reagents and solvents were used as obtained without further purification. MnCl₂.4H₂O (59 mg,0.3 mmol), H₄bta (76 mg, 0.3 mmol) and NaOH (24 mg, 0.6 mmol) were dissolved in 10 ml of distilled water. The mixture was sealed in a Teflon-lined stainless steel vessel and kept at 443 K for one week. The vessel was gradually cooled to room temperature, and brown crystals suitable for crystallographic analysis were obtained after two weeks. These latter crystals were filtered, washed with water, and dried in air. Yield: 32 mg (30%) based on Mn.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the polymeric layer for compound (I).
	Fig. 3. Crystal packing of the compound (I).

Poly[(µ₆-benzene-1,2,4,5-tetracarboxylato)bis(1,10- phenanthroline)dimanganese(II)] top

Crystal data top

[Mn₂(C₁₀H₂O₈)(C₁₂H₈N₂)₂]	F(000) = 728
M_r = 360.20	D_x = 1.800 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4526 reflections
a = 7.5115 (7) Å	θ = 3.3–26.0°
b = 19.8111 (19) Å	µ = 1.02 mm⁻¹
c = 9.6327 (9) Å	T = 293 K
β = 112.027 (2)°	Block, brown
V = 1328.8 (2) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Rigaku Scxmini 1K CCD area-detector diffractometer	2336 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
thin–slice ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −23→23
T_min = 0.796, T_max = 0.833	l = −11→10
8026 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0597P)²] where P = (F_o² + 2F_c²)/3
2336 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Mn₂(C₁₀H₂O₈)(C₁₂H₈N₂)₂]	V = 1328.8 (2) Å³
M_r = 360.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5115 (7) Å	µ = 1.02 mm⁻¹
b = 19.8111 (19) Å	T = 293 K
c = 9.6327 (9) Å	0.22 × 0.20 × 0.18 mm
β = 112.027 (2)°

Data collection top

Rigaku Scxmini 1K CCD area-detector diffractometer	2336 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1853 reflections with I > 2σ(I)
T_min = 0.796, T_max = 0.833	R_int = 0.057
8026 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	Δρ_max = 0.58 e Å⁻³
2336 reflections	Δρ_min = −0.35 e Å⁻³
217 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
Mn1	0.26486 (7)	0.43326 (2)	0.53505 (5)	0.01340 (18)
N1	0.4147 (4)	0.35226 (13)	0.4456 (3)	0.0176 (6)
N2	0.1642 (4)	0.33159 (13)	0.5808 (3)	0.0166 (6)
C1	0.5418 (5)	0.36248 (18)	0.3823 (4)	0.0230 (8)
H1A	0.5722	0.4067	0.3677	0.028*
C11	0.2366 (5)	0.27625 (16)	0.5373 (4)	0.0182 (7)
C2	0.6321 (5)	0.31037 (19)	0.3366 (4)	0.0282 (9)
H2A	0.7216	0.3200	0.2939	0.034*
C10	0.0358 (5)	0.32165 (18)	0.6425 (4)	0.0223 (8)
H10A	−0.0171	0.3591	0.6709	0.027*
C12	0.3729 (5)	0.28764 (16)	0.4675 (4)	0.0196 (8)
C7	0.1838 (5)	0.21006 (17)	0.5571 (4)	0.0255 (8)
C4	0.4550 (5)	0.23179 (18)	0.4230 (4)	0.0243 (8)
C3	0.5875 (5)	0.2453 (2)	0.3552 (4)	0.0285 (9)
H3A	0.6443	0.2100	0.3233	0.034*
C5	0.3984 (6)	0.16497 (18)	0.4459 (4)	0.0321 (10)
H5A	0.4519	0.1280	0.4165	0.039*
C9	−0.0232 (5)	0.2580 (2)	0.6666 (4)	0.0302 (9)
H9A	−0.1137	0.2535	0.7105	0.036*
C6	0.2683 (6)	0.15507 (18)	0.5097 (4)	0.0311 (10)
H6A	0.2333	0.1112	0.5230	0.037*
C8	0.0499 (6)	0.20273 (19)	0.6268 (4)	0.0336 (10)
H8A	0.0125	0.1600	0.6451	0.040*
C13	−0.0288 (4)	0.49094 (14)	0.1344 (3)	0.0097 (6)
C16	0.8525 (4)	0.48483 (15)	0.8620 (3)	0.0127 (7)
C14	−0.0734 (4)	0.48127 (16)	0.2744 (3)	0.0139 (7)
C17	0.6894 (4)	0.46887 (15)	0.7169 (3)	0.0138 (7)
C15	0.8273 (4)	0.47604 (15)	0.9971 (3)	0.0132 (7)
H15A	0.7104	0.4597	0.9953	0.020*
O1	−0.0214 (3)	0.42752 (11)	0.3466 (2)	0.0190 (5)
O4	0.5436 (3)	0.44168 (12)	0.7236 (2)	0.0225 (6)
O3	0.2918 (3)	0.51596 (11)	0.4038 (2)	0.0190 (5)
O2	0.1650 (3)	0.47176 (12)	0.6976 (2)	0.0235 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0180 (3)	0.0144 (3)	0.0099 (3)	−0.0002 (2)	0.0077 (2)	0.0001 (2)
N1	0.0191 (16)	0.0201 (16)	0.0154 (15)	0.0002 (12)	0.0083 (12)	−0.0011 (11)
N2	0.0205 (16)	0.0167 (15)	0.0139 (14)	0.0011 (12)	0.0079 (12)	0.0031 (11)
C1	0.023 (2)	0.029 (2)	0.0188 (19)	−0.0053 (16)	0.0099 (16)	−0.0061 (15)
C11	0.024 (2)	0.0169 (17)	0.0111 (17)	−0.0008 (14)	0.0040 (14)	0.0005 (13)
C2	0.026 (2)	0.036 (2)	0.028 (2)	0.0041 (17)	0.0160 (18)	−0.0040 (17)
C10	0.022 (2)	0.027 (2)	0.0185 (19)	−0.0010 (15)	0.0081 (16)	0.0020 (15)
C12	0.0224 (19)	0.0213 (19)	0.0112 (17)	0.0019 (14)	0.0018 (15)	−0.0004 (13)
C7	0.032 (2)	0.0211 (19)	0.0173 (19)	−0.0048 (16)	0.0028 (16)	0.0017 (14)
C4	0.027 (2)	0.0226 (19)	0.0153 (19)	0.0059 (15)	−0.0016 (15)	−0.0059 (14)
C3	0.028 (2)	0.037 (2)	0.0180 (19)	0.0140 (17)	0.0059 (16)	−0.0062 (17)
C5	0.046 (3)	0.019 (2)	0.023 (2)	0.0117 (18)	0.0043 (19)	−0.0017 (15)
C9	0.031 (2)	0.037 (2)	0.024 (2)	−0.0093 (18)	0.0124 (18)	0.0045 (17)
C6	0.052 (3)	0.0132 (18)	0.021 (2)	−0.0037 (17)	0.0054 (19)	0.0024 (14)
C8	0.043 (3)	0.024 (2)	0.028 (2)	−0.0164 (18)	0.0059 (19)	0.0072 (17)
C13	0.0145 (17)	0.0092 (15)	0.0080 (16)	0.0022 (12)	0.0072 (13)	0.0007 (11)
C16	0.0195 (18)	0.0104 (16)	0.0087 (16)	0.0019 (13)	0.0059 (13)	−0.0009 (12)
C14	0.0147 (17)	0.0180 (18)	0.0083 (16)	−0.0016 (14)	0.0037 (13)	−0.0028 (13)
C17	0.0152 (18)	0.0133 (16)	0.0133 (17)	0.0008 (14)	0.0060 (14)	−0.0013 (13)
C15	0.0138 (17)	0.0109 (16)	0.0169 (18)	−0.0037 (13)	0.0079 (14)	−0.0009 (13)
O1	0.0222 (13)	0.0204 (13)	0.0156 (12)	−0.0013 (10)	0.0086 (10)	0.0051 (10)
O4	0.0168 (13)	0.0371 (15)	0.0129 (12)	−0.0094 (11)	0.0046 (10)	−0.0013 (10)
O3	0.0248 (14)	0.0225 (13)	0.0097 (12)	−0.0064 (10)	0.0065 (10)	0.0032 (9)
O2	0.0300 (15)	0.0297 (14)	0.0166 (13)	0.0079 (11)	0.0154 (11)	−0.0008 (10)

Geometric parameters (Å, º) top

Mn1—O2	2.116 (2)	C4—C5	1.433 (5)
Mn1—O3	2.125 (2)	C3—H3A	0.9300
Mn1—O4	2.204 (2)	C5—C6	1.350 (5)
Mn1—O1	2.237 (2)	C5—H5A	0.9300
Mn1—N2	2.252 (3)	C9—C8	1.344 (5)
Mn1—N1	2.305 (3)	C9—H9A	0.9300
N1—C1	1.327 (4)	C6—H6A	0.9300
N1—C12	1.353 (4)	C8—H8A	0.9300
N2—C10	1.323 (4)	C13—C15ⁱ	1.390 (4)
N2—C11	1.358 (4)	C13—C16ⁱⁱ	1.397 (4)
C1—C2	1.394 (5)	C13—C14	1.518 (4)
C1—H1A	0.9300	C16—C15	1.394 (4)
C11—C7	1.404 (5)	C16—C13ⁱⁱ	1.397 (4)
C11—C12	1.438 (5)	C16—C17	1.506 (4)
C2—C3	1.360 (5)	C14—O2ⁱⁱⁱ	1.246 (4)
C2—H2A	0.9300	C14—O1	1.251 (4)
C10—C9	1.385 (5)	C17—O4	1.244 (4)
C10—H10A	0.9300	C17—O3ⁱⁱ	1.259 (4)
C12—C4	1.409 (5)	C15—C13^iv	1.390 (4)
C7—C8	1.410 (5)	C15—H15A	0.9300
C7—C6	1.420 (5)	O3—C17ⁱⁱ	1.259 (4)
C4—C3	1.406 (5)	O2—C14ⁱⁱⁱ	1.246 (4)

O2—Mn1—O3	107.56 (9)	C8—C7—C6	124.0 (3)
O2—Mn1—O4	81.59 (9)	C3—C4—C12	117.3 (3)
O3—Mn1—O4	99.15 (8)	C3—C4—C5	123.4 (3)
O2—Mn1—O1	96.86 (9)	C12—C4—C5	119.3 (3)
O3—Mn1—O1	80.40 (8)	C2—C3—C4	119.6 (3)
O4—Mn1—O1	178.19 (9)	C2—C3—H3A	120.2
O2—Mn1—N2	86.52 (9)	C4—C3—H3A	120.2
O3—Mn1—N2	156.89 (9)	C6—C5—C4	120.8 (3)
O4—Mn1—N2	101.02 (9)	C6—C5—H5A	119.6
O1—Mn1—N2	79.78 (9)	C4—C5—H5A	119.6
O2—Mn1—N1	152.37 (9)	C8—C9—C10	120.2 (3)
O3—Mn1—N1	98.36 (9)	C8—C9—H9A	119.9
O4—Mn1—N1	85.10 (9)	C10—C9—H9A	119.9
O1—Mn1—N1	96.70 (9)	C5—C6—C7	121.5 (3)
N2—Mn1—N1	72.38 (9)	C5—C6—H6A	119.2
C1—N1—C12	117.7 (3)	C7—C6—H6A	119.2
C1—N1—Mn1	127.0 (2)	C9—C8—C7	119.5 (3)
C12—N1—Mn1	115.2 (2)	C9—C8—H8A	120.2
C10—N2—C11	117.5 (3)	C7—C8—H8A	120.2
C10—N2—Mn1	125.1 (2)	C15ⁱ—C13—C16ⁱⁱ	119.2 (3)
C11—N2—Mn1	117.3 (2)	C15ⁱ—C13—C14	117.8 (3)
N1—C1—C2	123.5 (3)	C16ⁱⁱ—C13—C14	123.0 (3)
N1—C1—H1A	118.3	C15—C16—C13ⁱⁱ	118.6 (3)
C2—C1—H1A	118.3	C15—C16—C17	119.5 (3)
N2—C11—C7	123.1 (3)	C13ⁱⁱ—C16—C17	121.9 (3)
N2—C11—C12	117.1 (3)	O2ⁱⁱⁱ—C14—O1	126.7 (3)
C7—C11—C12	119.8 (3)	O2ⁱⁱⁱ—C14—C13	115.0 (3)
C3—C2—C1	119.1 (3)	O1—C14—C13	118.3 (3)
C3—C2—H2A	120.4	O4—C17—O3ⁱⁱ	123.8 (3)
C1—C2—H2A	120.4	O4—C17—C16	118.0 (3)
N2—C10—C9	123.0 (3)	O3ⁱⁱ—C17—C16	118.2 (3)
N2—C10—H10A	118.5	C13^iv—C15—C16	122.2 (3)
C9—C10—H10A	118.5	C13^iv—C15—H15A	118.9
N1—C12—C4	122.8 (3)	C16—C15—H15A	118.9
N1—C12—C11	118.0 (3)	C14—O1—Mn1	114.4 (2)
C4—C12—C11	119.2 (3)	C17—O4—Mn1	125.0 (2)
C11—C7—C8	116.7 (3)	C17ⁱⁱ—O3—Mn1	143.3 (2)
C11—C7—C6	119.3 (3)	C14ⁱⁱⁱ—O2—Mn1	143.9 (2)

O2—Mn1—N1—C1	−136.3 (3)	C1—C2—C3—C4	−1.4 (5)
O3—Mn1—N1—C1	23.6 (3)	C12—C4—C3—C2	0.6 (5)
O4—Mn1—N1—C1	−75.0 (3)	C5—C4—C3—C2	179.4 (3)
O1—Mn1—N1—C1	104.8 (3)	C3—C4—C5—C6	−179.0 (3)
N2—Mn1—N1—C1	−178.2 (3)	C12—C4—C5—C6	−0.2 (5)
O2—Mn1—N1—C12	40.5 (3)	N2—C10—C9—C8	−0.1 (5)
O3—Mn1—N1—C12	−159.7 (2)	C4—C5—C6—C7	−0.3 (6)
O4—Mn1—N1—C12	101.7 (2)	C11—C7—C6—C5	−0.1 (6)
O1—Mn1—N1—C12	−78.5 (2)	C8—C7—C6—C5	−178.8 (3)
N2—Mn1—N1—C12	−1.5 (2)	C10—C9—C8—C7	−1.5 (5)
O2—Mn1—N2—C10	20.7 (3)	C11—C7—C8—C9	1.7 (5)
O3—Mn1—N2—C10	−108.2 (3)	C6—C7—C8—C9	−179.5 (3)
O4—Mn1—N2—C10	101.4 (3)	C15ⁱ—C13—C14—O2ⁱⁱⁱ	−80.8 (4)
O1—Mn1—N2—C10	−77.0 (3)	C16ⁱⁱ—C13—C14—O2ⁱⁱⁱ	97.9 (4)
N1—Mn1—N2—C10	−177.4 (3)	C15ⁱ—C13—C14—O1	97.1 (4)
O2—Mn1—N2—C11	−161.6 (2)	C16ⁱⁱ—C13—C14—O1	−84.2 (4)
O3—Mn1—N2—C11	69.5 (3)	C15—C16—C17—O4	−7.3 (4)
O4—Mn1—N2—C11	−80.8 (2)	C13ⁱⁱ—C16—C17—O4	173.5 (3)
O1—Mn1—N2—C11	100.8 (2)	C15—C16—C17—O3ⁱⁱ	172.5 (3)
N1—Mn1—N2—C11	0.3 (2)	C13ⁱⁱ—C16—C17—O3ⁱⁱ	−6.8 (4)
C12—N1—C1—C2	0.6 (5)	C13ⁱⁱ—C16—C15—C13^iv	0.4 (5)
Mn1—N1—C1—C2	177.2 (3)	C17—C16—C15—C13^iv	−178.9 (3)
C10—N2—C11—C7	−1.1 (5)	O2ⁱⁱⁱ—C14—O1—Mn1	−88.5 (4)
Mn1—N2—C11—C7	−179.0 (3)	C13—C14—O1—Mn1	93.8 (3)
C10—N2—C11—C12	178.7 (3)	O2—Mn1—O1—C14	85.7 (2)
Mn1—N2—C11—C12	0.8 (4)	O3—Mn1—O1—C14	−21.1 (2)
N1—C1—C2—C3	0.9 (5)	N2—Mn1—O1—C14	170.9 (2)
C11—N2—C10—C9	1.4 (5)	N1—Mn1—O1—C14	−118.5 (2)
Mn1—N2—C10—C9	179.1 (2)	O3ⁱⁱ—C17—O4—Mn1	−13.7 (4)
C1—N1—C12—C4	−1.5 (5)	C16—C17—O4—Mn1	165.99 (19)
Mn1—N1—C12—C4	−178.6 (3)	O2—Mn1—O4—C17	−130.8 (3)
C1—N1—C12—C11	179.4 (3)	O3—Mn1—O4—C17	−24.2 (3)
Mn1—N1—C12—C11	2.4 (4)	N2—Mn1—O4—C17	144.5 (3)
N2—C11—C12—N1	−2.1 (5)	N1—Mn1—O4—C17	73.5 (3)
C7—C11—C12—N1	177.6 (3)	O2—Mn1—O3—C17ⁱⁱ	−164.7 (3)
N2—C11—C12—C4	178.8 (3)	O4—Mn1—O3—C17ⁱⁱ	111.3 (3)
C7—C11—C12—C4	−1.4 (5)	O1—Mn1—O3—C17ⁱⁱ	−70.5 (3)
N2—C11—C7—C8	−0.4 (5)	N2—Mn1—O3—C17ⁱⁱ	−39.2 (5)
C12—C11—C7—C8	179.8 (3)	N1—Mn1—O3—C17ⁱⁱ	25.0 (4)
N2—C11—C7—C6	−179.3 (3)	O3—Mn1—O2—C14ⁱⁱⁱ	25.6 (4)
C12—C11—C7—C6	0.9 (5)	O4—Mn1—O2—C14ⁱⁱⁱ	122.6 (4)
N1—C12—C4—C3	1.0 (5)	O1—Mn1—O2—C14ⁱⁱⁱ	−56.4 (4)
C11—C12—C4—C3	180.0 (3)	N2—Mn1—O2—C14ⁱⁱⁱ	−135.7 (4)
N1—C12—C4—C5	−178.0 (3)	N1—Mn1—O2—C14ⁱⁱⁱ	−175.3 (3)
C11—C12—C4—C5	1.1 (5)

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

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₀H₂O₈)(C₁₂H₈N₂)₂]
M_r	360.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5115 (7), 19.8111 (19), 9.6327 (9)
β (°)	112.027 (2)
V (Å³)	1328.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Scxmini 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.796, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	8026, 2336, 1853
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.107, 0.99
No. of reflections	2336
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.35

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—O2	2.116 (2)	Mn1—N2	2.252 (3)
Mn1—O3	2.125 (2)	Mn1—N1	2.305 (3)
Mn1—O4	2.204 (2)	O3—C17ⁱ	1.259 (4)
Mn1—O1	2.237 (2)	O2—C14ⁱⁱ	1.246 (4)

O2—Mn1—O3	107.56 (9)	O3—Mn1—N2	156.89 (9)
O2—Mn1—O4	81.59 (9)	O4—Mn1—N2	101.02 (9)
O3—Mn1—O4	99.15 (8)	O1—Mn1—N2	79.78 (9)
O2—Mn1—O1	96.86 (9)	O3—Mn1—N1	98.36 (9)
O3—Mn1—O1	80.40 (8)	O4—Mn1—N1	85.10 (9)
O4—Mn1—O1	178.19 (9)	O1—Mn1—N1	96.70 (9)
O2—Mn1—N2	86.52 (9)	N2—Mn1—N1	72.38 (9)

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

References

Aghabozorg, H., Bahrami, Z., Tabatabaie, M., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m2022–m2023. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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