Crystal structure of poly[(N,N-di­methyl­acetamide-κO)(μ4-5-methyl­isophthalato-κ5O:O,O′:O′′:O′′′)manganese(II)]

Jin, L.; Zha, L.-L.; Gao, S.; Yang, S.-Y.; Huang, R.-B.

doi:10.1107/S2056989014025626

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages m1-m2

https://doi.org/10.1107/S2056989014025626

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Crystal structure of poly[(N,N-dimethylacetamide-κO)(μ₄-5-methylisophthalato-κ⁵O:O,O′:O′′:O′′′)manganese(II)]

Lan Jin,^a Li-Li Zha,^a San Gao,^a Shi-Yao Yang ^a ^* and Rong-Bin Huang ^a

^aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: syyang@xmu.edu.cn

Edited by U. Flörke, University of Paderborn, Germany (Received 19 November 2014; accepted 23 November 2014; online 1 January 2015)

The title compound, poly[(N,N-dimethylacetamide-κO)(μ₄-5-methylisophthalato-κ⁵O,O′:O′,O′′:O′′)manganese(II)], [Mn(C₉H₆O₄)(C₃H₇NO)]_n, was obtained from a mixture containing MnCl₂·4H₂O and 5-methylisophthalic acid in N,N-dimethylacetamide solution. The Mn²⁺ ion is coordinated by five O atoms from four bridging 5-methylisophthalate ligands and one O atom from one N,N-dimethylacetamide ligand, defining a considerably distorted coordination polyhedron with one very long Mn—O bond of 2.623 (2) Å. The Mn²⁺ ions are joined by carboxylate groups, forming rod-shaped secondary building units along the a axis. The rods are further connected by 5-methylisophthalate ligands to form the pcu (primitive cubic net) structure.

Keywords: crystal structure; manganese(II) coordination polymer; pcu structure; N,N-dimethylacetamide; 5-methylisophthalate.

CCDC reference: 1035658

1. Related literature

For the structures of coordination polymers comprising first-row transition metal ions and benzene dicarboxylates, see: Deng et al. (2013 ); Jin et al. (2012 ); Li et al. (2010 ); Yang et al. (2013 ); Zhou et al. (2009 ). For the nomenclature for metal-organic frameworks, see: Rosi et al. (2005 );. A very closely related crystal structure, poly[(dimethylformamide)(5-methoxybenzene-1,3-dicarboxylato)manganese(II)], was reported recently (Huang, 2013 ). The author described the structure in a PtS (cooperite) topology according to a different analytical approach (Carlucci et al., 2003 ; Hill et al., 2005 ).

2. Experimental

2.1. Crystal data

[Mn(C₉H₆O₄)(C₃H₇NO)]
M_r = 306.17
Orthorhombic, P n a 2₁
a = 7.281 (5) Å
b = 15.148 (11) Å
c = 10.903 (8) Å
V = 1202.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 200 K
0.15 × 0.10 × 0.10 mm

2.2. Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.851, T_max = 0.897
10159 measured reflections
2874 independent reflections
2768 reflections with I > 2σ(I)
R_int = 0.025

2.3. Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.059
S = 1.07
2874 reflections
175 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 0 Friedel pairs
Absolute structure parameter: 0.025 (14)

Table 1
Selected geometric parameters (Å, °)

Mn1—O4ⁱ	2.0609 (19)
Mn1—O3ⁱⁱ	2.0855 (15)
Mn1—O1	2.0885 (16)
Mn1—O5	2.1342 (18)
Mn1—O2ⁱⁱⁱ	2.1378 (16)

O4ⁱ—Mn1—O3ⁱⁱ	131.59 (6)
O4ⁱ—Mn1—O1	83.59 (6)
O3ⁱⁱ—Mn1—O1	98.77 (7)
O4ⁱ—Mn1—O5	83.95 (6)
O3ⁱⁱ—Mn1—O5	84.88 (7)
O1—Mn1—O5	166.04 (5)
O4ⁱ—Mn1—O2ⁱⁱⁱ	135.70 (6)
O3ⁱⁱ—Mn1—O2ⁱⁱⁱ	92.23 (7)
O1—Mn1—O2ⁱⁱⁱ	97.51 (7)
O5—Mn1—O2ⁱⁱⁱ	95.80 (7)
Symmetry codes: (i) $[-x, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1035658

Crystal structure: contains datablocks I, AE2. DOI: https://doi.org/10.1107/S2056989014025626/fk2084sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014025626/fk2084Isup2.hkl

checkCIF report

Structural commentary top

We have reported the structures of dozens of coordination polymers comprising first-row transition metal ions and benzene dicarboxylates (Deng et al., 2013; Jin et al., 2012; Li et al. 2010; Yang et al., 2013; Zhou et al., 2009). We found that metal ion is the most important factor that influences the structure of coordination polymer.

The title compound, [Mn(C₉H₆O₄)(C₃H₇O)]_n, (I) was obtained with the same method reported in our previous paper (Yang et al., 2013). The structure feature of I is quite similar to those manganese analogs reported in that paper. The Mn²⁺ ions are joined by carboxyl groups to form rod-shaped secondary building units (SBUs) along the a axis. Each rod is further connected to four adjacent rods by 5-methylisophthalates to form the rod packing type 2 pcu (primitive cubic net) structure according to the nomenclature for metal-organic frameworks (Rosi et al., 2005). A very closely related molecular structure, poly[(dimethylformamide)(5-methoxybenzene-1,3-dicarboxylato)manganese(II)], was reported recently (Huang, 2013). The author described the structure in PtS (cooperite) topology according to a different analysis approach (Carlucci et al., 2003; Hill et al., 2005).

Synthesis and crystallization top

A mixture containing MnCl₂.4H₂O (0.039 g, 0.20 mmol) and 5-methylisophthalic acid (H₂mip, 0.036 g, 0.20 mmol) in 10 mL N,N-dimethylacetamide (DMF) was heated at 100 °C for 5000 min. Colourless block crystals were generated (0.025 g, 41%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms were positioned geometrically and refined using a riding model (including free rotation about the C—C bond), with C—H = 0.95–0.99 Å and with U_iso(H) = 1.2 (1.5 for methyl groups) times U_eq(C).

Related literature top

For the structures of coordination polymers comprising first-row transition metal ions and benzene dicarboxylates, see: Deng et al. (2013); Jin et al. (2012); Li et al. (2010); Yang et al. (2013); Zhou et al. (2009). For the nomenclature for metal-organic frameworks, see: Rosi et al. (2005);. A very closely related crystal structure, poly[(dimethylformamide)(5-methoxybenzene-1,3-dicarboxylato)manganese(II)], was reported recently (Huang, 2013). The author described the structure in a PtS (cooperite) topology according to a different analytical approach (Carlucci et al., 2003; Hill et al., 2005).

Structure description top

For the structures of coordination polymers comprising first-row transition metal ions and benzene dicarboxylates, see: Deng et al. (2013); Jin et al. (2012); Li et al. (2010); Yang et al. (2013); Zhou et al. (2009). For the nomenclature for metal-organic frameworks, see: Rosi et al. (2005);. A very closely related crystal structure, poly[(dimethylformamide)(5-methoxybenzene-1,3-dicarboxylato)manganese(II)], was reported recently (Huang, 2013). The author described the structure in a PtS (cooperite) topology according to a different analytical approach (Carlucci et al., 2003; Hill et al., 2005).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Coordination modes in (I). Anisotropic displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: i -x, -y + 2, z + 1/2; ii -x + 1/2, y - 1/2, z + 1/2; iii x - 1/2, -y + 3/2, z; iv x + 1/2, -y + 3/2, z; v -x + 1/2, y + 1/2, z - 1/2; vi -x, -y + 2, z - 1/2.
	Fig. 2. The packing of (I), viewed down the a axis, showing MnO₆ in polyhedra.

Poly[(N,N-dimethylacetamide-κO)(µ₄-5-methylisophthalato-κ⁵O:O,O':O'':O''')manganese(II)] top

Crystal data top

[Mn(C₉H₆O₄)(C₃H₇NO)]	F(000) = 628
M_r = 306.17	D_x = 1.691 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6647 reflections
a = 7.281 (5) Å	θ = 2.3–28.7°
b = 15.148 (11) Å	µ = 1.11 mm⁻¹
c = 10.903 (8) Å	T = 200 K
V = 1202.5 (15) Å³	Rod, colorless
Z = 4	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker APEX area-detector diffractometer	2874 independent reflections
Radiation source: fine-focus sealed tube	2768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scan	θ_max = 29.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.851, T_max = 0.897	k = −19→19
10159 measured reflections	l = −13→14

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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0316P)² + 0.1079P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2874 reflections	Δρ_max = 0.26 e Å⁻³
175 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 0 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.025 (14)

Crystal data top

[Mn(C₉H₆O₄)(C₃H₇NO)]	V = 1202.5 (15) Å³
M_r = 306.17	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.281 (5) Å	µ = 1.11 mm⁻¹
b = 15.148 (11) Å	T = 200 K
c = 10.903 (8) Å	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker APEX area-detector diffractometer	2874 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2768 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.897	R_int = 0.025
10159 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	Δρ_max = 0.26 e Å⁻³
S = 1.07	Δρ_min = −0.29 e Å⁻³
2874 reflections	Absolute structure: Flack (1983), 0 Friedel pairs
175 parameters	Absolute structure parameter: 0.025 (14)
1 restraint

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	0.02668 (3)	0.718473 (13)	0.40075 (4)	0.01733 (7)
O1	0.21890 (19)	0.76885 (7)	0.27699 (13)	0.0264 (3)
O2	0.40794 (19)	0.87833 (8)	0.28213 (14)	0.0320 (3)
O3	0.30783 (16)	1.12474 (7)	−0.01315 (13)	0.0244 (3)
O4	0.02059 (16)	1.15017 (8)	−0.06146 (13)	0.0254 (3)
O5	−0.15683 (19)	0.69631 (9)	0.55025 (14)	0.0301 (3)
N1	−0.2451 (2)	0.61847 (11)	0.71232 (16)	0.0323 (4)
C1	0.1457 (2)	0.89377 (11)	0.16063 (16)	0.0210 (3)
C2	0.1976 (2)	0.97512 (10)	0.11805 (18)	0.0208 (3)
H2A	0.3104	1.0003	0.1442	0.025*
C3	0.0878 (2)	1.02002 (10)	0.03817 (16)	0.0196 (3)
C4	−0.0754 (2)	0.98383 (11)	0.00205 (17)	0.0237 (3)
H4A	−0.1529	1.0157	−0.0523	0.028*
C5	−0.1290 (3)	0.90257 (12)	0.04273 (18)	0.0269 (4)
C6	−0.0157 (3)	0.85839 (12)	0.12133 (19)	0.0261 (4)
H6A	−0.0505	0.8014	0.1494	0.031*
C7	0.2643 (2)	0.84485 (11)	0.24625 (17)	0.0236 (4)
C8	0.1438 (2)	1.10570 (10)	−0.01549 (17)	0.0197 (3)
C9	−0.3076 (3)	0.86426 (15)	0.0039 (3)	0.0448 (6)
H9A	−0.2980	0.7997	0.0020	0.067*
H9B	−0.3392	0.8861	−0.0780	0.067*
H9C	−0.4034	0.8817	0.0623	0.067*
C10	−0.1507 (3)	0.63087 (12)	0.61313 (19)	0.0282 (4)
H10A	−0.0704	0.5849	0.5880	0.034*
C11	−0.2297 (3)	0.53842 (16)	0.7799 (2)	0.0459 (6)
H11A	−0.1283	0.5032	0.7469	0.069*
H11B	−0.3446	0.5050	0.7731	0.069*
H11C	−0.2057	0.5520	0.8664	0.069*
C12	−0.3792 (4)	0.68114 (17)	0.7505 (3)	0.0545 (7)
H12A	−0.3596	0.7369	0.7069	0.082*
H12B	−0.3680	0.6911	0.8390	0.082*
H12C	−0.5022	0.6586	0.7319	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01845 (11)	0.01338 (10)	0.02015 (12)	0.00142 (7)	0.00145 (16)	0.00084 (12)
O1	0.0343 (7)	0.0170 (5)	0.0279 (7)	0.0074 (5)	0.0119 (6)	0.0068 (5)
O2	0.0262 (7)	0.0330 (7)	0.0368 (8)	−0.0002 (6)	−0.0060 (6)	0.0145 (6)
O3	0.0188 (6)	0.0207 (5)	0.0336 (7)	−0.0019 (4)	0.0012 (5)	0.0087 (5)
O4	0.0232 (6)	0.0172 (6)	0.0359 (8)	0.0006 (4)	−0.0074 (5)	0.0059 (5)
O5	0.0333 (7)	0.0266 (6)	0.0305 (8)	0.0002 (6)	0.0079 (6)	0.0069 (6)
N1	0.0328 (9)	0.0366 (9)	0.0274 (10)	−0.0036 (7)	0.0051 (7)	0.0065 (7)
C1	0.0227 (8)	0.0191 (7)	0.0211 (8)	0.0021 (6)	0.0043 (6)	0.0043 (6)
C2	0.0192 (8)	0.0193 (7)	0.0240 (8)	0.0002 (6)	0.0026 (6)	0.0021 (6)
C3	0.0202 (8)	0.0175 (7)	0.0212 (8)	0.0010 (6)	0.0047 (7)	0.0019 (6)
C4	0.0217 (8)	0.0230 (8)	0.0264 (9)	0.0006 (6)	0.0005 (7)	0.0053 (7)
C5	0.0267 (9)	0.0274 (9)	0.0267 (9)	−0.0067 (7)	−0.0001 (7)	0.0044 (7)
C6	0.0295 (9)	0.0201 (8)	0.0286 (10)	−0.0051 (6)	0.0048 (7)	0.0040 (7)
C7	0.0262 (8)	0.0235 (8)	0.0213 (9)	0.0070 (7)	0.0060 (7)	0.0051 (7)
C8	0.0223 (8)	0.0168 (7)	0.0199 (8)	0.0008 (6)	0.0000 (6)	0.0005 (6)
C9	0.0371 (12)	0.0452 (12)	0.0521 (14)	−0.0188 (9)	−0.0127 (10)	0.0132 (11)
C10	0.0253 (9)	0.0291 (9)	0.0303 (10)	−0.0008 (7)	0.0022 (8)	0.0026 (8)
C11	0.0445 (13)	0.0526 (13)	0.0407 (14)	−0.0074 (10)	0.0018 (11)	0.0222 (11)
C12	0.0674 (17)	0.0524 (14)	0.0437 (15)	0.0092 (13)	0.0238 (13)	−0.0037 (12)

Geometric parameters (Å, º) top

Mn1—O4ⁱ	2.0609 (19)	C2—C3	1.364 (2)
Mn1—O3ⁱⁱ	2.0855 (15)	C2—H2A	0.9500
Mn1—O1	2.0885 (16)	C3—C4	1.367 (2)
Mn1—O5	2.1342 (18)	C3—C8	1.481 (2)
Mn1—O2ⁱⁱⁱ	2.1378 (16)	C4—C5	1.365 (2)
O1—C7	1.244 (2)	C4—H4A	0.9500
O2—C7	1.226 (2)	C5—C6	1.365 (3)
O2—Mn1^iv	2.1378 (16)	C5—C9	1.485 (3)
O3—C8	1.229 (2)	C6—H6A	0.9500
O3—Mn1^v	2.0855 (15)	C9—H9A	0.9800
O4—C8	1.228 (2)	C9—H9B	0.9800
O4—Mn1^vi	2.0609 (18)	C9—H9C	0.9800
O5—C10	1.206 (2)	C10—H10A	0.9500
N1—C10	1.295 (3)	C11—H11A	0.9800
N1—C11	1.424 (3)	C11—H11B	0.9800
N1—C12	1.424 (3)	C11—H11C	0.9800
C1—C6	1.361 (3)	C12—H12A	0.9800
C1—C2	1.370 (2)	C12—H12B	0.9800
C1—C7	1.472 (2)	C12—H12C	0.9800

O4ⁱ—Mn1—O3ⁱⁱ	131.59 (6)	C4—C5—C9	120.65 (19)
O4ⁱ—Mn1—O1	83.59 (6)	C1—C6—C5	121.77 (17)
O3ⁱⁱ—Mn1—O1	98.77 (7)	C1—C6—H6A	119.1
O4ⁱ—Mn1—O5	83.95 (6)	C5—C6—H6A	119.1
O3ⁱⁱ—Mn1—O5	84.88 (7)	O2—C7—O1	121.56 (17)
O1—Mn1—O5	166.04 (5)	O2—C7—C1	119.62 (16)
O4ⁱ—Mn1—O2ⁱⁱⁱ	135.70 (6)	O1—C7—C1	118.76 (17)
O3ⁱⁱ—Mn1—O2ⁱⁱⁱ	92.23 (7)	O4—C8—O3	126.10 (17)
O1—Mn1—O2ⁱⁱⁱ	97.51 (7)	O4—C8—C3	116.16 (16)
O5—Mn1—O2ⁱⁱⁱ	95.80 (7)	O3—C8—C3	117.70 (15)
C7—O1—Mn1	133.66 (12)	C5—C9—H9A	109.5
C7—O2—Mn1^iv	104.72 (11)	C5—C9—H9B	109.5
C8—O3—Mn1^v	135.39 (11)	H9A—C9—H9B	109.5
C8—O4—Mn1^vi	137.13 (12)	C5—C9—H9C	109.5
C10—O5—Mn1	122.70 (13)	H9A—C9—H9C	109.5
C10—N1—C11	120.94 (19)	H9B—C9—H9C	109.5
C10—N1—C12	120.75 (18)	O5—C10—N1	125.04 (18)
C11—N1—C12	118.1 (2)	O5—C10—H10A	117.5
C6—C1—C2	119.04 (17)	N1—C10—H10A	117.5
C6—C1—C7	120.53 (16)	N1—C11—H11A	109.5
C2—C1—C7	120.42 (17)	N1—C11—H11B	109.5
C3—C2—C1	120.22 (17)	H11A—C11—H11B	109.5
C3—C2—H2A	119.9	N1—C11—H11C	109.5
C1—C2—H2A	119.9	H11A—C11—H11C	109.5
C2—C3—C4	119.58 (15)	H11B—C11—H11C	109.5
C2—C3—C8	121.87 (16)	N1—C12—H12A	109.5
C4—C3—C8	118.50 (15)	N1—C12—H12B	109.5
C5—C4—C3	121.09 (17)	H12A—C12—H12B	109.5
C5—C4—H4A	119.5	N1—C12—H12C	109.5
C3—C4—H4A	119.5	H12A—C12—H12C	109.5
C6—C5—C4	118.27 (17)	H12B—C12—H12C	109.5
C6—C5—C9	121.07 (18)

O4ⁱ—Mn1—O1—C7	−2.37 (18)	Mn1^iv—O2—C7—O1	−2.1 (2)
O3ⁱⁱ—Mn1—O1—C7	−133.56 (19)	Mn1^iv—O2—C7—C1	−179.51 (13)
O5—Mn1—O1—C7	−29.3 (4)	Mn1—O1—C7—O2	104.6 (2)
O2ⁱⁱⁱ—Mn1—O1—C7	132.99 (19)	Mn1—O1—C7—C1	−78.0 (2)
O4ⁱ—Mn1—O5—C10	−152.61 (17)	C6—C1—C7—O2	−178.90 (18)
O3ⁱⁱ—Mn1—O5—C10	−19.79 (16)	C2—C1—C7—O2	2.0 (3)
O1—Mn1—O5—C10	−125.7 (2)	C6—C1—C7—O1	3.7 (3)
O2ⁱⁱⁱ—Mn1—O5—C10	71.94 (17)	C2—C1—C7—O1	−175.45 (17)
C6—C1—C2—C3	0.5 (3)	Mn1^vi—O4—C8—O3	−26.5 (3)
C7—C1—C2—C3	179.64 (16)	Mn1^vi—O4—C8—C3	155.59 (13)
C1—C2—C3—C4	0.8 (3)	Mn1^v—O3—C8—O4	−12.1 (3)
C1—C2—C3—C8	−176.42 (16)	Mn1^v—O3—C8—C3	165.74 (13)
C2—C3—C4—C5	−1.3 (3)	C2—C3—C8—O4	−163.04 (17)
C8—C3—C4—C5	176.03 (17)	C4—C3—C8—O4	19.7 (2)
C3—C4—C5—C6	0.4 (3)	C2—C3—C8—O3	18.9 (2)
C3—C4—C5—C9	179.3 (2)	C4—C3—C8—O3	−158.37 (17)
C2—C1—C6—C5	−1.4 (3)	Mn1—O5—C10—N1	172.24 (15)
C7—C1—C6—C5	179.47 (18)	C11—N1—C10—O5	179.4 (2)
C4—C5—C6—C1	0.9 (3)	C12—N1—C10—O5	5.1 (3)
C9—C5—C6—C1	−178.0 (2)

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

Selected geometric parameters (Å, º) top

Mn1—O4ⁱ	2.0609 (19)	Mn1—O5	2.1342 (18)
Mn1—O3ⁱⁱ	2.0855 (15)	Mn1—O2ⁱⁱⁱ	2.1378 (16)
Mn1—O1	2.0885 (16)

O4ⁱ—Mn1—O3ⁱⁱ	131.59 (6)	O1—Mn1—O5	166.04 (5)
O4ⁱ—Mn1—O1	83.59 (6)	O4ⁱ—Mn1—O2ⁱⁱⁱ	135.70 (6)
O3ⁱⁱ—Mn1—O1	98.77 (7)	O3ⁱⁱ—Mn1—O2ⁱⁱⁱ	92.23 (7)
O4ⁱ—Mn1—O5	83.95 (6)	O1—Mn1—O2ⁱⁱⁱ	97.51 (7)
O3ⁱⁱ—Mn1—O5	84.88 (7)	O5—Mn1—O2ⁱⁱⁱ	95.80 (7)

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

Acknowledgements

We are grateful for financial support by the National Natural Science Foundation of China (grant Nos. 21071117 and 21471125).

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Volume 71| Part 1| January 2015| Pages m1-m2

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