Poly[bis­[μ-1,4-bis­(1H-imidazol-5-yl)benzene-κ2N3:N3′]diformatomanganese(II)]

Chen, S.-S.; Yang, S.-L.; Zhang, S.-P.; Lu, Z.-Q.

doi:10.1107/S1600536810044053

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1501-m1502

https://doi.org/10.1107/S1600536810044053

Open

access

Poly[bis[μ-1,4-bis(1H-imidazol-5-yl)benzene-κ²N³:N^3′]diformatomanganese(II)]

Shui-Sheng Chen,^a ^* Sen-Lin Yang,^a Shu-Ping Zhang ^a and Zi-Qiang Lu ^b

^aDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China, and ^bKey Laboratory of Functional Organometallic Materials, Department of Chemistry and Materials Science, Hengyang Normal University, Luoyang, Henan 471022, People's Republic of China
^*Correspondence e-mail: sscfync@163.com

(Received 29 September 2010; accepted 28 October 2010; online 6 November 2010)

In the title compound, [Mn(CHO₂)₂(C₁₂H₁₀N₄)₂]_n, the Mn^II atom and the benzene ring of the ligand lie on an inversion centers. The Mn^II atom has an octahedral coordination environment composed of four N atoms from two different symmetry-related N-heterocyclic ligands forming the basal plane, and two O atoms from symmetry-related formate anions occupying the apical positions. The title compound forms a two-dimensional (4,4) net parallel to (100) with all the Mn^II atoms lying on a plane. The crystal structure is consolidated by intermolecular N—H⋯O hydrogen bonds..

Related literature

For related literature on transition metal complex assembly, see: Kitagawa & Kondo (1998 ). For related literature on novel coordination networks belonging to entangled systems, see: Batten & Robson (1998 ); Hoskins et al. (1997a ,b ). For a related Mn^II complex, see: Zhao et al. (2009 ); Zhu et al. (2010 ). For three-dimensional structures, see: Tian et al. (2007 ).

Experimental

Crystal data

[Mn(CHO₂)₂(C₁₂H₁₀N₄)₂]
M_r = 565.46
Monoclinic, P 2₁ /c
a = 7.3240 (8) Å
b = 12.1313 (13) Å
c = 14.1802 (15) Å
β = 100.704 (2)°
V = 1238.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 293 K
0.21 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.887, T_max = 0.933
6495 measured reflections
2420 independent reflections
2196 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.06
2420 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.00	2.840 (2)	165
N4—H4⋯O2ⁱⁱ	0.86	1.95	2.736 (2)	151
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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 global, I. DOI: https://doi.org/10.1107/S1600536810044053/bx2313sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044053/bx2313Isup2.hkl

checkCIF report

Comment top

Recently, a great deal of interest in transition metal complex assembly has been devoted to the development of rational synthetic routes to novel crystal frameworks, due to their potential applications in many areas (Kitagawa et al., 1998). So far large quantities of novel coordination networks belonging to entangled systems have been reported in the literature (Batten et al., 1998). It has been demostrated that the flexible bridging ligand can easily construct entangled systems. For example, 1,4-bix(imidazol-1-yl-methyl) benzene (bix) formed an infinite polyrotaxane network of [Ag₂(bix)₃(NO₃)₂] by reactions with silver nitrate (Hoskins et al., 1997a) and gave a two-dimensional interpenetrated network of [Zn(bix)₂(NO₃)₂.4.5H₂O] by reactions with zinc nitrate which has both polyrotaxane and polycatenane characters (Hoskins et al., 1997b). As an extension of above work, we report a new entangled metal complex [Mn(C₂₄H₂₀N₈)₂(HCOO)₂]_n (I) based on rigid 1,4-di(1H-imidazol-4-yl)benzene ligand (L) and metal Mn^II salts. In the title compound, the Mn ^II atom and the ring benzene of the ligand are lies on inversion center. The Mn^II has an octahedral coordination environment surrounded by four nitrogen atoms from two different N-heterocyclic ligands symmetry-related forming the basal plane and two oxygen donors from one formate anion symmetry-related occupying the apical positions (Fig. 1). The Mn—N distances are comparable to those found in other crystallographically characterized Mn^II complex (Zhao et al., 2009) and Mn—O distance is coincident with another Mn^II complex (Zhu et al., 2010). The title compound form two-dimensional (4,4) net and its building unit is [Mn(L)]. The Mn^II are connected to a 1D linear chain along b-axis. The ligand, L, link Mn^IIions in adjacent chains by the same mode as described above, which makes the Mn^IIions links another 1D chain along c-axis. Therefore, the title compound is further connect to a 2D infinite strucure in bc plane, Fig. 2. The void spaces within the [Mn(L)₂]_n coordination polymer layers permit mutual inclined two parallel sets of layers to angle into three dimensional framework (Tian et al., 2007) (Fig. 3). The crystal structure of the title compound is stabilized by two intermolecular N—H···O interactions with average H···O distances 2.00 Å and N—H···O angles in the range 151-165°.

Related literature top

For related literature on transition metal complex assembly, see: Kitagawa & Kondo (1998). For related literature on novel coordination networks belonging to entangled systems, see: Batten & Robson (1998); Hoskins et al. (1997a,b). For a related Mn^II complex, see Zhao et al. (2009); Zhu et al. (2010). For related literature on [subject?], see: Tian et al. (2007).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. A mixture containing MnCl₂.4H₂O (19.8 mg, 0.05 mmol), L (27.6 mg, 0.1 mmol), DMF (N:N'- dimethylformamide, 1 mL), 10 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated at 393 K for 72 h. After cooling to room temperature within 12 h, block brown crystals of (I) suitable for X-ray diffraction analysis were obtained in 69% Yield.

Structure description top

For related literature on transition metal complex assembly, see: Kitagawa & Kondo (1998). For related literature on novel coordination networks belonging to entangled systems, see: Batten & Robson (1998); Hoskins et al. (1997a,b). For a related Mn^II complex, see Zhao et al. (2009); Zhu et al. (2010). For related literature on [subject?], see: Tian et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. Symmetry codes: (i) 1-x, 1-y, 1-z.
	Fig. 2. Two-dimensional (4,4) rectangular grid [Mn(L)₂]_n coordination polymer layer motif along the bc plane of the compound (I).
	Fig. 3. The three-dimensional structure built from two-dimension mutual inclined interpenetration of the compound (I).

Poly[bis[µ-1,4-bis(1H-imidazol-5-yl)benzene- κ²N³:N^3']diformatomanganese(II)] top

Crystal data top

[Mn(CHO₂)₂(C₂₄H₂₀N₈)₂]	F(000) = 582
M_r = 565.46	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3510 reflections
a = 7.3240 (8) Å	θ = 2.2–28.2°
b = 12.1313 (13) Å	µ = 0.59 mm⁻¹
c = 14.1802 (15) Å	T = 293 K
β = 100.704 (2)°	Block, brown
V = 1238.0 (2) Å³	0.21 × 0.16 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD diffractometer	2420 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→4
T_min = 0.887, T_max = 0.933	k = −14→14
6495 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0581P)² + 0.230P] where P = (F_o² + 2F_c²)/3
2420 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Mn(CHO₂)₂(C₂₄H₂₀N₈)₂]	V = 1238.0 (2) Å³
M_r = 565.46	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3240 (8) Å	µ = 0.59 mm⁻¹
b = 12.1313 (13) Å	T = 293 K
c = 14.1802 (15) Å	0.21 × 0.16 × 0.12 mm
β = 100.704 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2420 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2196 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.933	R_int = 0.043
6495 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2420 reflections	Δρ_min = −0.25 e Å⁻³
178 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	0.7024 (3)	0.61227 (17)	0.34180 (14)	0.0363 (5)
H1	0.7649	0.6613	0.3869	0.044*
C2	0.5906 (3)	0.53538 (16)	0.20304 (13)	0.0292 (4)
C3	0.5424 (3)	0.47633 (17)	0.27654 (14)	0.0319 (5)
H3	0.4721	0.4120	0.2690	0.038*
C4	0.5462 (3)	0.51810 (15)	0.09923 (14)	0.0265 (4)
C5	0.5767 (3)	0.59952 (16)	0.03487 (13)	0.0289 (4)
H5	0.6284	0.6666	0.0576	0.035*
C6	0.5306 (3)	0.58109 (16)	−0.06262 (13)	0.0298 (4)
H6	0.5514	0.6364	−0.1048	0.036*
C7	0.2276 (3)	0.66265 (16)	0.35944 (15)	0.0386 (5)
H7	0.2459	0.6234	0.3056	0.046*
C8	0.1345 (3)	0.79075 (15)	0.44854 (14)	0.0292 (4)
C9	0.2315 (3)	0.71098 (15)	0.50414 (14)	0.0323 (4)
H9	0.2541	0.7105	0.5709	0.039*
C10	0.0609 (3)	0.89682 (15)	0.47356 (14)	0.0290 (4)
C11	−0.0078 (3)	0.97491 (17)	0.40435 (16)	0.0351 (5)
H11	−0.0133	0.9588	0.3398	0.042*
C12	−0.0679 (3)	1.07637 (16)	0.43069 (15)	0.0355 (5)
H12	−0.1139	1.1276	0.3834	0.043*
C13	0.1608 (3)	0.36826 (16)	0.37714 (14)	0.0339 (5)
H13	0.0769	0.4215	0.3893	0.041*
Mn1	0.5000	0.5000	0.5000	0.02250 (15)
N1	0.6124 (3)	0.52515 (14)	0.36355 (12)	0.0330 (4)
N2	0.6934 (3)	0.62227 (14)	0.24675 (11)	0.0351 (4)
H2	0.7431	0.6738	0.2183	0.042*
N3	0.2911 (2)	0.63150 (13)	0.44833 (12)	0.0317 (4)
N4	0.1335 (2)	0.75759 (14)	0.35583 (12)	0.0350 (4)
H4	0.0817	0.7917	0.3047	0.042*
O1	0.3183 (2)	0.37154 (11)	0.42634 (10)	0.0378 (4)
O2	0.1041 (2)	0.30061 (13)	0.31300 (11)	0.0461 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0449 (12)	0.0407 (11)	0.0220 (10)	−0.0042 (10)	0.0024 (9)	−0.0056 (8)
C2	0.0326 (10)	0.0325 (10)	0.0223 (10)	0.0011 (8)	0.0050 (8)	−0.0028 (8)
C3	0.0420 (12)	0.0318 (10)	0.0222 (10)	−0.0031 (9)	0.0068 (9)	−0.0030 (8)
C4	0.0282 (10)	0.0307 (9)	0.0206 (9)	0.0025 (8)	0.0048 (8)	−0.0009 (7)
C5	0.0344 (11)	0.0270 (9)	0.0245 (10)	−0.0020 (8)	0.0035 (8)	−0.0031 (7)
C6	0.0363 (11)	0.0309 (10)	0.0225 (9)	−0.0007 (8)	0.0061 (8)	0.0037 (7)
C7	0.0481 (13)	0.0319 (11)	0.0323 (11)	0.0115 (10)	−0.0014 (9)	−0.0050 (9)
C8	0.0278 (10)	0.0256 (9)	0.0326 (10)	0.0020 (8)	0.0016 (8)	−0.0003 (8)
C9	0.0405 (11)	0.0295 (10)	0.0261 (10)	0.0054 (9)	0.0037 (8)	0.0000 (8)
C10	0.0247 (9)	0.0247 (9)	0.0367 (11)	0.0029 (7)	0.0031 (8)	0.0002 (8)
C11	0.0402 (12)	0.0338 (10)	0.0305 (10)	0.0067 (9)	0.0044 (9)	−0.0008 (8)
C12	0.0394 (12)	0.0306 (10)	0.0346 (11)	0.0096 (9)	0.0024 (9)	0.0069 (8)
C13	0.0388 (12)	0.0284 (10)	0.0331 (11)	0.0017 (9)	0.0029 (9)	−0.0045 (8)
Mn1	0.0303 (3)	0.0201 (2)	0.0153 (2)	0.00383 (15)	−0.00031 (16)	−0.00102 (13)
N1	0.0423 (10)	0.0362 (9)	0.0204 (8)	−0.0006 (8)	0.0059 (7)	−0.0017 (7)
N2	0.0465 (10)	0.0377 (9)	0.0210 (8)	−0.0095 (8)	0.0056 (7)	−0.0013 (7)
N3	0.0395 (10)	0.0266 (8)	0.0267 (8)	0.0088 (7)	0.0000 (7)	−0.0006 (6)
N4	0.0411 (10)	0.0305 (9)	0.0285 (9)	0.0102 (7)	−0.0062 (7)	0.0025 (7)
O1	0.0427 (9)	0.0303 (8)	0.0348 (8)	−0.0038 (6)	−0.0075 (7)	−0.0042 (6)
O2	0.0523 (10)	0.0427 (9)	0.0351 (9)	−0.0002 (7)	−0.0131 (7)	−0.0127 (7)

Geometric parameters (Å, º) top

C1—N1	1.312 (3)	C9—N3	1.369 (2)
C1—N2	1.343 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C12ⁱⁱ	1.388 (3)
C2—C3	1.364 (3)	C10—C11	1.389 (3)
C2—N2	1.375 (3)	C11—C12	1.382 (3)
C2—C4	1.462 (3)	C11—H11	0.9300
C3—N1	1.379 (3)	C12—C10ⁱⁱ	1.388 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C6ⁱ	1.388 (3)	C13—O1	1.233 (2)
C4—C5	1.391 (3)	C13—O2	1.238 (2)
C5—C6	1.379 (3)	C13—H13	0.9300
C5—H5	0.9300	Mn1—O1	2.1848 (13)
C6—C4ⁱ	1.388 (3)	Mn1—O1ⁱⁱⁱ	2.1848 (13)
C6—H6	0.9300	Mn1—N3ⁱⁱⁱ	2.2376 (16)
C7—N3	1.315 (3)	Mn1—N3	2.2376 (16)
C7—N4	1.338 (2)	Mn1—N1	2.2597 (17)
C7—H7	0.9300	Mn1—N1ⁱⁱⁱ	2.2597 (17)
C8—C9	1.362 (3)	N2—H2	0.8600
C8—N4	1.373 (3)	N4—H4	0.8600
C8—C10	1.464 (3)

N1—C1—N2	112.07 (18)	C11—C12—H12	119.4
N1—C1—H1	124.0	C10ⁱⁱ—C12—H12	119.4
N2—C1—H1	124.0	O1—C13—O2	126.0 (2)
C3—C2—N2	104.84 (17)	O1—C13—H13	117.0
C3—C2—C4	130.79 (19)	O2—C13—H13	117.0
N2—C2—C4	124.36 (17)	O1—Mn1—O1ⁱⁱⁱ	180.0
C2—C3—N1	110.64 (18)	O1—Mn1—N3ⁱⁱⁱ	88.09 (6)
C2—C3—H3	124.7	O1ⁱⁱⁱ—Mn1—N3ⁱⁱⁱ	91.91 (6)
N1—C3—H3	124.7	O1—Mn1—N3	91.91 (6)
C6ⁱ—C4—C5	118.28 (17)	O1ⁱⁱⁱ—Mn1—N3	88.09 (6)
C6ⁱ—C4—C2	119.98 (17)	N3ⁱⁱⁱ—Mn1—N3	180.00 (8)
C5—C4—C2	121.74 (17)	O1—Mn1—N1	88.47 (6)
C6—C5—C4	120.23 (18)	O1ⁱⁱⁱ—Mn1—N1	91.53 (6)
C6—C5—H5	119.9	N3ⁱⁱⁱ—Mn1—N1	92.34 (6)
C4—C5—H5	119.9	N3—Mn1—N1	87.66 (6)
C5—C6—C4ⁱ	121.50 (17)	O1—Mn1—N1ⁱⁱⁱ	91.53 (6)
C5—C6—H6	119.3	O1ⁱⁱⁱ—Mn1—N1ⁱⁱⁱ	88.47 (6)
C4ⁱ—C6—H6	119.3	N3ⁱⁱⁱ—Mn1—N1ⁱⁱⁱ	87.66 (6)
N3—C7—N4	111.81 (18)	N3—Mn1—N1ⁱⁱⁱ	92.34 (6)
N3—C7—H7	124.1	N1—Mn1—N1ⁱⁱⁱ	180.0
N4—C7—H7	124.1	C1—N1—C3	104.77 (17)
C9—C8—N4	104.81 (16)	C1—N1—Mn1	126.06 (13)
C9—C8—C10	131.31 (18)	C3—N1—Mn1	125.06 (14)
N4—C8—C10	123.55 (17)	C1—N2—C2	107.68 (16)
C8—C9—N3	110.71 (17)	C1—N2—H2	126.2
C8—C9—H9	124.6	C2—N2—H2	126.2
N3—C9—H9	124.6	C7—N3—C9	104.94 (16)
C12ⁱⁱ—C10—C11	118.30 (18)	C7—N3—Mn1	128.10 (14)
C12ⁱⁱ—C10—C8	119.65 (17)	C9—N3—Mn1	125.79 (13)
C11—C10—C8	121.96 (19)	C7—N4—C8	107.72 (17)
C12—C11—C10	120.5 (2)	C7—N4—H4	126.1
C12—C11—H11	119.7	C8—N4—H4	126.1
C10—C11—H11	119.7	C13—O1—Mn1	135.75 (13)
C11—C12—C10ⁱⁱ	121.16 (18)

N2—C2—C3—N1	0.3 (2)	O1ⁱⁱⁱ—Mn1—N1—C3	−172.33 (16)
C4—C2—C3—N1	−178.5 (2)	N3ⁱⁱⁱ—Mn1—N1—C3	95.69 (16)
C3—C2—C4—C6ⁱ	−12.5 (3)	N3—Mn1—N1—C3	−84.31 (16)
N2—C2—C4—C6ⁱ	168.97 (19)	N1—C1—N2—C2	−0.1 (2)
C3—C2—C4—C5	166.7 (2)	C3—C2—N2—C1	−0.1 (2)
N2—C2—C4—C5	−11.9 (3)	C4—C2—N2—C1	178.79 (19)
C6ⁱ—C4—C5—C6	0.2 (3)	N4—C7—N3—C9	0.7 (2)
C2—C4—C5—C6	−178.98 (18)	N4—C7—N3—Mn1	−167.33 (14)
C4—C5—C6—C4ⁱ	−0.2 (3)	C8—C9—N3—C7	−0.9 (2)
N4—C8—C9—N3	0.8 (2)	C8—C9—N3—Mn1	167.49 (13)
C10—C8—C9—N3	−172.7 (2)	O1—Mn1—N3—C7	−63.64 (19)
C9—C8—C10—C12ⁱⁱ	−7.5 (3)	O1ⁱⁱⁱ—Mn1—N3—C7	116.36 (19)
N4—C8—C10—C12ⁱⁱ	−179.89 (19)	N1—Mn1—N3—C7	24.74 (18)
C9—C8—C10—C11	169.0 (2)	N1ⁱⁱⁱ—Mn1—N3—C7	−155.26 (18)
N4—C8—C10—C11	−3.4 (3)	O1—Mn1—N3—C9	130.62 (16)
C12ⁱⁱ—C10—C11—C12	−0.2 (3)	O1ⁱⁱⁱ—Mn1—N3—C9	−49.38 (16)
C8—C10—C11—C12	−176.81 (19)	N1—Mn1—N3—C9	−140.99 (17)
C10—C11—C12—C10ⁱⁱ	0.3 (4)	N1ⁱⁱⁱ—Mn1—N3—C9	39.01 (17)
N2—C1—N1—C3	0.3 (2)	N3—C7—N4—C8	−0.3 (2)
N2—C1—N1—Mn1	−157.68 (15)	C9—C8—N4—C7	−0.3 (2)
C2—C3—N1—C1	−0.3 (2)	C10—C8—N4—C7	173.77 (19)
C2—C3—N1—Mn1	157.90 (14)	O2—C13—O1—Mn1	151.13 (17)
O1—Mn1—N1—C1	161.35 (18)	N3ⁱⁱⁱ—Mn1—O1—C13	178.4 (2)
O1ⁱⁱⁱ—Mn1—N1—C1	−18.65 (18)	N3—Mn1—O1—C13	−1.6 (2)
N3ⁱⁱⁱ—Mn1—N1—C1	−110.62 (18)	N1—Mn1—O1—C13	−89.2 (2)
N3—Mn1—N1—C1	69.38 (18)	N1ⁱⁱⁱ—Mn1—O1—C13	90.8 (2)
O1—Mn1—N1—C3	7.67 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^iv	0.86	2.00	2.840 (2)	165
N4—H4···O2^v	0.86	1.95	2.736 (2)	151

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

Experimental details

Crystal data
Chemical formula	[Mn(CHO₂)₂(C₂₄H₂₀N₈)₂]
M_r	565.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.3240 (8), 12.1313 (13), 14.1802 (15)
β (°)	100.704 (2)
V (Å³)	1238.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.21 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.887, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	6495, 2420, 2196
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.06
No. of reflections	2420
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), 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
N2—H2···O2ⁱ	0.86	2.00	2.840 (2)	165.00
N4—H4···O2ⁱⁱ	0.86	1.95	2.736 (2)	151.00

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

Acknowledgements

This work was supported by the Natural Science Foundation of Anhui Provincial Education Commission (grant No. Kj2009A047Zc), the Construct Program of the Key Discipline in Henan Province, Luoyang Bureau of Science and Technology (grant No. 2009 K J29) and the Research Award Fund for Outstanding Young Teachers of Henan Province (2008).

References

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494. Web of Science CrossRef Google Scholar
Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hoskins, B. F., Robson, R. & Slizys, D. A. (1997a). Angew. Chem. Int. Ed. 36, 2336–2338. CrossRef CAS Google Scholar
Hoskins, B. F., Robson, R. & Slizys, D. A. (1997b). J. Am. Chem. Soc. 119, 2952–2953. CSD CrossRef CAS Web of Science Google Scholar
Kitagawa, S. & Kondo, M. (1998). Bull. Chem. Soc. Jpn, 71, 1739–1753. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Z. F., Lin, J. G., Su, Y., Wen, L. L., Liu, Y. M., Zhu, H. Z. & Meng, Q. J. (2007). Cryst. Growth Des. 7, 1863–1867. Web of Science CSD CrossRef CAS Google Scholar
Zhao, J., Zheng, X.-G. & Hu, Z.-Z. (2009). Acta Cryst. E65, m1642. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, L., Wang, D. & Xu, H. (2010). Acta Cryst. E66, m513. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.