catena-Poly[[[2-(1,3-thia-zol-4-yl)-1H-benzimidazole]-manganese(II)]-μ-oxalato].

In the title compound, [Mn(C2O4)(C10H7N3S)] n , the Mn(II) cation is chelated by one 2-(1,3-thia-zol-4-yl)-1H-benzimidazole ligand and two oxalate anions in a distorted N2O4 octa-hedral geometry. Two independent oxalate anions are located on individual inversion centers and bridge the Mn(II) cations into a polymeric chain running along [101]. The thia-zole ring is approximately coplanar with the benzimidazole ring system [dihedral angle = 4.19 (9)°]. In the crystal, classical N-H⋯O hydrogen bonds and weak C-H⋯O hydrogen bonds link the polymeric chains into a three-dimensional supra-molecular architecture.

Related literature

For applications of thia­bendazole compounds, see: Yu et al. (2002 ▶); Devereux et al. (2004 ▶). For related structures, see: Wisniewski et al. (2001 ▶); Jean et al. (2002 ▶).

Experimental

Crystal data

[Mn(C2O4)(C10H7N3S)]

M = 344.21

Monoclinic,

a = 9.374 (2) Å

b = 17.834 (5) Å

c = 8.926 (2) Å

β = 113.500 (3)°

V = 1368.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.14 mm−1

T = 296 K

0.19 × 0.15 × 0.12 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.813, T max = 0.876

7273 measured reflections

2412 independent reflections

2221 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.069

S = 1.08

2412 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813023428/xu5729sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023428/xu5729Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023428/xu5729Isup3.cdx

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

[Mn(C2O4)(C10H7N3S)]	F(000) = 692
Mr = 344.21	Dx = 1.671 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5023 reflections
a = 9.374 (2) Å	θ = 2.4–28.3°
b = 17.834 (5) Å	µ = 1.14 mm−1
c = 8.926 (2) Å	T = 296 K
β = 113.500 (3)°	Block, colorless
V = 1368.5 (6) Å3	0.19 × 0.15 × 0.12 mm
Z = 4

Bruker SMART 1000 diffractometer	2412 independent reflections
Radiation source: fine-focus sealed tube	2221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→11
Tmin = 0.813, Tmax = 0.876	k = −21→20
7273 measured reflections	l = −10→10

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.5684P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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
Mn1	0.28290 (3)	0.932763 (14)	0.20300 (3)	0.03109 (11)
S1	0.64896 (7)	0.83770 (4)	−0.00986 (9)	0.0624 (2)
O1	0.39555 (17)	0.91664 (7)	0.47096 (16)	0.0433 (4)
O2	0.43698 (18)	1.03068 (8)	0.29932 (16)	0.0484 (4)
O3	0.17776 (14)	0.99693 (8)	−0.02014 (16)	0.0376 (3)
O4	0.05151 (15)	0.95656 (8)	0.18979 (16)	0.0377 (3)
N1	0.45900 (19)	0.87876 (9)	0.1125 (2)	0.0413 (4)
N2	0.22949 (18)	0.81054 (8)	0.17676 (18)	0.0320 (3)
N3	0.2776 (2)	0.69534 (9)	0.1121 (2)	0.0397 (4)
H3	0.3214	0.6596	0.0814	0.048*
C1	0.0364 (2)	1.01176 (9)	−0.0610 (2)	0.0304 (4)
C2	0.3161 (2)	0.76883 (10)	0.1233 (2)	0.0322 (4)
C3	0.1257 (2)	0.76095 (10)	0.1997 (2)	0.0345 (4)
C4	0.4377 (2)	0.80249 (11)	0.0832 (2)	0.0356 (4)
C5	0.4889 (2)	0.96704 (10)	0.5512 (2)	0.0336 (4)
C6	0.1543 (2)	0.68852 (11)	0.1592 (2)	0.0408 (5)
C7	0.0076 (2)	0.77466 (13)	0.2539 (3)	0.0445 (5)
H7	−0.0116	0.8225	0.2831	0.053*
C8	0.0644 (3)	0.62731 (13)	0.1659 (3)	0.0615 (7)
H8	0.0825	0.5792	0.1372	0.074*
C9	0.5322 (3)	0.77105 (13)	0.0185 (3)	0.0480 (5)
H9	0.5331	0.7205	−0.0067	0.058*
C10	−0.0793 (3)	0.71361 (15)	0.2620 (3)	0.0602 (7)
H10	−0.1583	0.7206	0.2986	0.072*
C11	−0.0529 (3)	0.64235 (16)	0.2177 (4)	0.0697 (8)
H11	−0.1164	0.6033	0.2230	0.084*
C12	0.5678 (3)	0.90352 (14)	0.0683 (3)	0.0537 (6)
H12	0.5982	0.9535	0.0791	0.064*

	U11	U22	U33	U12	U13	U23
Mn1	0.02973 (17)	0.02287 (16)	0.03696 (18)	−0.00105 (10)	0.00938 (13)	−0.00085 (10)
S1	0.0522 (4)	0.0722 (4)	0.0788 (4)	0.0189 (3)	0.0429 (3)	0.0219 (3)
O1	0.0519 (9)	0.0291 (7)	0.0401 (7)	−0.0171 (6)	0.0090 (6)	0.0016 (6)
O2	0.0616 (9)	0.0343 (8)	0.0363 (8)	−0.0179 (7)	0.0058 (7)	0.0050 (6)
O3	0.0294 (7)	0.0425 (8)	0.0417 (7)	0.0018 (6)	0.0150 (6)	0.0054 (6)
O4	0.0372 (7)	0.0387 (7)	0.0376 (7)	0.0065 (6)	0.0152 (6)	0.0074 (6)
N1	0.0368 (9)	0.0326 (9)	0.0584 (11)	0.0025 (7)	0.0230 (8)	0.0052 (8)
N2	0.0325 (8)	0.0247 (8)	0.0367 (8)	−0.0019 (6)	0.0115 (6)	−0.0021 (6)
N3	0.0472 (10)	0.0238 (8)	0.0445 (9)	0.0038 (7)	0.0144 (8)	−0.0033 (7)
C1	0.0323 (10)	0.0224 (8)	0.0359 (10)	−0.0023 (7)	0.0130 (8)	−0.0040 (7)
C2	0.0340 (10)	0.0263 (9)	0.0327 (9)	0.0030 (7)	0.0095 (8)	−0.0013 (7)
C3	0.0330 (10)	0.0316 (10)	0.0335 (9)	−0.0042 (8)	0.0074 (8)	0.0026 (7)
C4	0.0340 (10)	0.0345 (10)	0.0357 (10)	0.0069 (8)	0.0112 (8)	0.0025 (8)
C5	0.0364 (10)	0.0219 (9)	0.0385 (10)	−0.0045 (7)	0.0106 (8)	0.0016 (8)
C6	0.0419 (11)	0.0293 (10)	0.0425 (11)	−0.0030 (8)	0.0077 (9)	0.0046 (8)
C7	0.0372 (11)	0.0505 (13)	0.0446 (11)	0.0007 (9)	0.0149 (9)	0.0096 (9)
C8	0.0638 (16)	0.0319 (12)	0.0713 (16)	−0.0098 (11)	0.0086 (13)	0.0109 (11)
C9	0.0470 (12)	0.0478 (13)	0.0505 (12)	0.0133 (10)	0.0208 (10)	0.0022 (10)
C10	0.0439 (13)	0.0677 (17)	0.0672 (15)	−0.0024 (12)	0.0203 (11)	0.0300 (13)
C11	0.0503 (15)	0.0589 (17)	0.0879 (19)	−0.0153 (12)	0.0149 (14)	0.0341 (14)
C12	0.0404 (12)	0.0462 (12)	0.0781 (16)	0.0069 (10)	0.0276 (11)	0.0182 (12)

Mn1—O1	2.2146 (15)	C1—O4ii	1.251 (2)
Mn1—O2	2.2100 (14)	C1—C1ii	1.556 (4)
Mn1—O3	2.1640 (14)	C2—C4	1.453 (3)
Mn1—O4	2.1667 (15)	C3—C6	1.396 (3)
Mn1—N1	2.3170 (17)	C3—C7	1.396 (3)
Mn1—N2	2.2279 (16)	C4—C9	1.357 (3)
S1—C12	1.694 (3)	C5—O2i	1.235 (2)
S1—C9	1.702 (2)	C5—C5i	1.553 (3)
O1—C5	1.260 (2)	C6—C8	1.395 (3)
O2—C5i	1.235 (2)	C7—C10	1.378 (3)
O3—C1	1.254 (2)	C7—H7	0.9300
O4—C1ii	1.251 (2)	C8—C11	1.378 (4)
N1—C12	1.308 (3)	C8—H8	0.9300
N1—C4	1.384 (3)	C9—H9	0.9300
N2—C2	1.323 (2)	C10—C11	1.382 (4)
N2—C3	1.389 (2)	C10—H10	0.9300
N3—C2	1.353 (2)	C11—H11	0.9300
N3—C6	1.384 (3)	C12—H12	0.9300
N3—H3	0.8600
O3—Mn1—O4	76.57 (5)	N2—C2—C4	120.73 (16)
O3—Mn1—O2	85.83 (5)	N3—C2—C4	126.47 (17)
O4—Mn1—O2	110.56 (6)	N2—C3—C6	109.46 (17)
O3—Mn1—O1	155.34 (5)	N2—C3—C7	129.70 (18)
O4—Mn1—O1	96.90 (5)	C6—C3—C7	120.84 (19)
O2—Mn1—O1	74.11 (5)	C9—C4—N1	114.63 (19)
O3—Mn1—N2	114.83 (5)	C9—C4—C2	130.04 (19)
O4—Mn1—N2	90.45 (6)	N1—C4—C2	115.32 (16)
O2—Mn1—N2	153.97 (6)	O2i—C5—O1	127.00 (17)
O1—Mn1—N2	88.68 (5)	O2i—C5—C5i	117.4 (2)
O3—Mn1—N1	91.44 (6)	O1—C5—C5i	115.6 (2)
O4—Mn1—N1	154.07 (6)	N3—C6—C8	132.4 (2)
O2—Mn1—N1	91.04 (6)	N3—C6—C3	105.50 (16)
O1—Mn1—N1	102.91 (6)	C8—C6—C3	122.1 (2)
N2—Mn1—N1	73.63 (6)	C10—C7—C3	116.5 (2)
C12—S1—C9	90.09 (11)	C10—C7—H7	121.7
C5—O1—Mn1	116.44 (11)	C3—C7—H7	121.7
C5i—O2—Mn1	116.44 (12)	C11—C8—C6	116.0 (2)
C1—O3—Mn1	114.82 (12)	C11—C8—H8	122.0
C1ii—O4—Mn1	114.64 (12)	C6—C8—H8	122.0
C12—N1—C4	110.24 (18)	C4—C9—S1	110.03 (17)
C12—N1—Mn1	135.57 (15)	C4—C9—H9	125.0
C4—N1—Mn1	113.89 (12)	S1—C9—H9	125.0
C2—N2—C3	105.18 (15)	C7—C10—C11	122.3 (2)
C2—N2—Mn1	116.34 (12)	C7—C10—H10	118.8
C3—N2—Mn1	138.48 (13)	C11—C10—H10	118.8
C2—N3—C6	107.05 (16)	C8—C11—C10	122.2 (2)
C2—N3—H3	126.5	C8—C11—H11	118.9
C6—N3—H3	126.5	C10—C11—H11	118.9
O4ii—C1—O3	126.52 (17)	N1—C12—S1	115.01 (18)
O4ii—C1—C1ii	116.9 (2)	N1—C12—H12	122.5
O3—C1—C1ii	116.54 (19)	S1—C12—H12	122.5
N2—C2—N3	112.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1iii	0.86	1.96	2.812 (2)	170
C12—H12···O3iv	0.93	2.52	3.137 (3)	124

Table 1

Selected bond lengths (Å)

Mn1—O1	2.2146 (15)
Mn1—O2	2.2100 (14)
Mn1—O3	2.1640 (14)
Mn1—O4	2.1667 (15)
Mn1—N1	2.3170 (17)
Mn1—N2	2.2279 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.86	1.96	2.812 (2)	170
C12—H12⋯O3ii	0.93	2.52	3.137 (3)	124

Symmetry codes: (i) ; (ii) .