Poly[(μ(4)-biphenyl-3,3'-dicarboxyl-ato)bis[μ(2)-1,1'-(butane-1,4-di-yl)diimidazole](μ(2)-oxalato)dimanganese(II)].

In the title coordination compound, [Mn(2)(C(14)H(8)O(4))(C(2)O(4))(C(10)H(14)N(4))(2)](n), the biphenyl-3,3'-dicarboxyl-ate 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-di-yl)diimidazole ligand coordinates to two Mn(II) atoms located in adjacent layers via Mn-N coordination bonds, giving a three-dimensional network. As the methyl-ene groups can bend freely relative to each other due to the C atoms connected via single bonds, the 1,1'-(butane-1,4-di-yl)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)(C10n class="Species">H14N4)2]

M = 818.60

Triclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.091

S = 1.01

3063 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −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 ▶).

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

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

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

[Mn2(C14H8O4)(C2O4)(C10H14N4)2]	Z = 1
Mr = 818.60	F(000) = 422
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0337P)2 + 0.7805P] where P = (Fo2 + 2Fc2)/3
3063 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.35 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	0.7299 (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)

	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)

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—N1iv	2.263 (2)
C9—N4	1.368 (4)	N1—Mn1v	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—N1iv	85.82 (9)
N3—C7—H7A	109.1	O4iii—Mn1—N1iv	90.21 (9)
C6—C7—H7A	109.1	O2—Mn1—N1iv	87.83 (9)
N3—C7—H7B	109.1	O1i—Mn1—N1iv	91.42 (9)
C6—C7—H7B	109.1	N4—Mn1—N1iv	178.50 (9)
H7A—C7—H7B	107.9	C1—N1—C2	104.3 (3)
C9—C8—N3	106.0 (3)	C1—N1—Mn1v	125.1 (2)
C9—C8—H8	127.0	C2—N1—Mn1v	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—Mn1v	−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—Mn1v	168.3 (3)	N1iv—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)	N1iv—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)