Poly[bis-[μ-1,4-bis-(1H-imidazol-5-yl)benzene-κN:N]diformatomanganese(II)].

In the title compound, [Mn(CHO(2))(2)(C(12)H(10)N(4))(2)](n), the Mn(II) atom and the benzene ring of the ligand lie on an inversion centers. The Mn(II) atom has an octa-hedral 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 inter-molecular 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 MnII 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 = 565.46

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.06

2420 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.25 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044053/bx2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044053/bx2313Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(CHO2)2(C24H20N8)2]	F(000) = 582
Mr = 565.46	Dx = 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

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

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(Fo2) + (0.0581P)2 + 0.230P] where P = (Fo2 + 2Fc2)/3
2420 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2iv	0.86	2.00	2.840 (2)	165
N4—H4···O2v	0.86	1.95	2.736 (2)	151

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) ; (ii) .