catena-Poly[[bis-(ethanol-κO)mangan-ese(II)]-μ-2,5-di-chloro-3,6-di-oxo-cyclo-hexa-1,4-diene-1,4-bis-(olato)-κ(4) O (1),O (6):O (3),O (4)].

In the title coordination polymer, [Mn(C6Cl2O4)(C2H5OH)2] n , the Mn(II) atom and the chloranilate [systematic name: 2,5-di-chloro-3,6-dioxo-cyclo-hexa-1,4-diene-1,4-bis-(olate)] ion lie on crystallographic inversion centers. The geometry around the Mn(II) atom is a distorted octa-hedron involving four O atoms of two chloranilate ions and two O atoms from two ethanol mol-ecules. The chloranilate ion serves as a bridging ligand between the Mn(II) ions, leading to an infinite linear chain along the b-axis direction. The chains are linked by O-H⋯O hydrogen bonds between the apically coordinating ethanol mol-ecule and the chloranilate ion, affording a two-dimensional layer expanding parallel to the ab plane.

Related literature

For metal complexes of chloranilic acid, see: Kawata et al. (1995 ▶, 1998 ▶); Kitagawa et al. (1996 ▶); Kitagawa & Kawata (2002 ▶); Abrahams et al. (2011 ▶).

Experimental

Crystal data

[Mn(C6Cl2O4)(C2H6O)2]

M = 354.05

Triclinic,

a = 5.0784 (5) Å

b = 8.1255 (8) Å

c = 8.9003 (9) Å

α = 102.718 (4)°

β = 105.175 (5)°

γ = 101.092 (3)°

V = 333.35 (6) Å3

Z = 1

Mo Kα radiation

μ = 1.41 mm−1

T = 200 K

0.50 × 0.25 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.406, T max = 0.869

3298 measured reflections

1534 independent reflections

1434 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.095

S = 1.17

1534 reflections

93 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.32 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2002 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814002396/is5335sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002396/is5335Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Mn(C6Cl2O4)(C2H6O)2]	Z = 1
Mr = 354.05	F(000) = 179.00
Triclinic, P1	Dx = 1.764 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 5.0784 (5) Å	Cell parameters from 3040 reflections
b = 8.1255 (8) Å	θ = 3.1–27.5°
c = 8.9003 (9) Å	µ = 1.41 mm−1
α = 102.718 (4)°	T = 200 K
β = 105.175 (5)°	Block, green
γ = 101.092 (3)°	0.50 × 0.25 × 0.10 mm
V = 333.35 (6) Å3

Rigaku R-AXIS RAPID II diffractometer	1434 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1	Rint = 0.029
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −6→6
Tmin = 0.406, Tmax = 0.869	k = −10→9
3298 measured reflections	l = −11→11
1534 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0437P] where P = (Fo2 + 2Fc2)/3
1534 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Mn1	1.0000	1.0000	0.0000	0.01772 (15)
Cl1	0.38362 (8)	0.36866 (5)	−0.26023 (5)	0.02047 (16)
O1	1.2640 (3)	0.84608 (14)	0.10826 (15)	0.0196 (3)
O2	0.7400 (3)	0.73489 (15)	−0.09699 (15)	0.0197 (3)
O3	0.8359 (3)	1.03778 (16)	0.20763 (16)	0.0256 (3)
C1	1.1523 (3)	0.68293 (19)	0.06530 (18)	0.0154 (3)
C2	0.8514 (3)	0.6189 (2)	−0.05794 (18)	0.0152 (3)
C3	0.7193 (4)	0.43901 (19)	−0.11994 (19)	0.0162 (3)
C4	0.8660 (5)	1.2048 (3)	0.3176 (3)	0.0278 (4)
C5	0.7319 (5)	1.1860 (4)	0.4470 (3)	0.0426 (6)
H1	0.691 (7)	0.975 (4)	0.187 (4)	0.049 (8)*
H4A	0.7772	1.2778	0.2552	0.0334*
H4B	1.0697	1.2656	0.3696	0.0334*
H5A	0.5295	1.1279	0.3960	0.0511*
H5B	0.7570	1.3021	0.5189	0.0511*
H5C	0.8219	1.1158	0.5104	0.0511*

	U11	U22	U33	U12	U13	U23
Mn1	0.0186 (3)	0.0085 (2)	0.0267 (3)	0.00490 (15)	0.00650 (16)	0.00590 (15)
Cl1	0.0161 (3)	0.0159 (3)	0.0247 (3)	0.00325 (16)	0.00050 (17)	0.00448 (17)
O1	0.0177 (6)	0.0086 (5)	0.0296 (7)	0.0025 (5)	0.0034 (5)	0.0055 (5)
O2	0.0183 (6)	0.0107 (6)	0.0296 (7)	0.0049 (5)	0.0041 (5)	0.0078 (5)
O3	0.0236 (7)	0.0177 (6)	0.0340 (7)	0.0020 (6)	0.0125 (6)	0.0037 (5)
C1	0.0157 (8)	0.0110 (7)	0.0204 (8)	0.0039 (6)	0.0071 (6)	0.0043 (6)
C2	0.0149 (7)	0.0128 (7)	0.0204 (8)	0.0051 (6)	0.0069 (6)	0.0065 (6)
C3	0.0148 (7)	0.0109 (7)	0.0215 (8)	0.0035 (6)	0.0033 (6)	0.0049 (6)
C4	0.0275 (10)	0.0221 (9)	0.0308 (10)	0.0060 (7)	0.0092 (8)	0.0022 (7)
C5	0.0331 (11)	0.0515 (14)	0.0345 (12)	0.0023 (10)	0.0145 (9)	−0.0018 (10)

Mn1—O1	2.1884 (13)	C1—C2	1.5410 (19)
Mn1—O1i	2.1884 (13)	C1—C3ii	1.392 (3)
Mn1—O2	2.1491 (11)	C2—C3	1.402 (2)
Mn1—O2i	2.1491 (11)	C4—C5	1.504 (4)
Mn1—O3	2.2042 (16)	O3—H1	0.76 (3)
Mn1—O3i	2.2042 (16)	C4—H4A	0.990
Cl1—C3	1.7285 (15)	C4—H4B	0.990
O1—C1	1.2646 (18)	C5—H5A	0.980
O2—C2	1.255 (3)	C5—H5B	0.980
O3—C4	1.442 (3)	C5—H5C	0.980
O1—Mn1—O1i	180.00 (7)	O2—C2—C1	116.48 (13)
O1—Mn1—O2	75.40 (5)	O2—C2—C3	124.00 (13)
O1—Mn1—O2i	104.60 (5)	C1—C2—C3	119.52 (15)
O1—Mn1—O3	89.94 (6)	Cl1—C3—C1ii	119.54 (10)
O1—Mn1—O3i	90.06 (6)	Cl1—C3—C2	119.10 (13)
O1i—Mn1—O2	104.60 (5)	C1ii—C3—C2	121.29 (13)
O1i—Mn1—O2i	75.40 (5)	O3—C4—C5	112.07 (17)
O1i—Mn1—O3	90.06 (6)	Mn1—O3—H1	112 (3)
O1i—Mn1—O3i	89.94 (6)	C4—O3—H1	112 (3)
O2—Mn1—O2i	180.00 (8)	O3—C4—H4A	109.195
O2—Mn1—O3	90.47 (5)	O3—C4—H4B	109.194
O2—Mn1—O3i	89.53 (5)	C5—C4—H4A	109.198
O2i—Mn1—O3	89.53 (5)	C5—C4—H4B	109.199
O2i—Mn1—O3i	90.47 (5)	H4A—C4—H4B	107.893
O3—Mn1—O3i	180.00 (7)	C4—C5—H5A	109.468
Mn1—O1—C1	115.42 (10)	C4—C5—H5B	109.470
Mn1—O2—C2	116.70 (9)	C4—C5—H5C	109.467
Mn1—O3—C4	125.08 (13)	H5A—C5—H5B	109.476
O1—C1—C2	115.83 (15)	H5A—C5—H5C	109.471
O1—C1—C3ii	125.09 (13)	H5B—C5—H5C	109.475
C2—C1—C3ii	119.07 (13)
O1—Mn1—O2—C2	−3.21 (9)	O3—Mn1—O2i—C2i	−86.98 (10)
O2—Mn1—O1—C1	0.99 (9)	O2i—Mn1—O3i—C4i	165.27 (10)
O1—Mn1—O2i—C2i	−176.79 (9)	O3i—Mn1—O2i—C2i	93.02 (10)
O2i—Mn1—O1—C1	−179.01 (9)	Mn1—O1—C1—C2	0.92 (19)
O1—Mn1—O3—C4	119.34 (10)	Mn1—O1—C1—C3ii	−179.43 (11)
O3—Mn1—O1—C1	91.49 (10)	Mn1—O2—C2—C1	4.67 (19)
O1—Mn1—O3i—C4i	60.66 (10)	Mn1—O2—C2—C3	−175.03 (11)
O3i—Mn1—O1—C1	−88.51 (10)	Mn1—O3—C4—C5	−179.70 (9)
O1i—Mn1—O2—C2	176.79 (9)	O1—C1—C2—O2	−3.8 (3)
O2—Mn1—O1i—C1i	179.01 (9)	O1—C1—C2—C3	175.92 (15)
O1i—Mn1—O2i—C2i	3.21 (9)	O1—C1—C3ii—Cl1ii	1.2 (3)
O2i—Mn1—O1i—C1i	−0.99 (9)	O1—C1—C3ii—C2ii	−175.82 (16)
O1i—Mn1—O3—C4	−60.66 (10)	C2—C1—C3ii—Cl1ii	−179.14 (13)
O3—Mn1—O1i—C1i	88.51 (10)	C2—C1—C3ii—C2ii	3.8 (3)
O1i—Mn1—O3i—C4i	−119.34 (10)	C3ii—C1—C2—O2	176.54 (15)
O3i—Mn1—O1i—C1i	−91.49 (10)	C3ii—C1—C2—C3	−3.7 (3)
O2—Mn1—O3—C4	−165.27 (10)	O2—C2—C3—Cl1	0.6 (3)
O3—Mn1—O2—C2	−93.02 (10)	O2—C2—C3—C1ii	−176.48 (16)
O2—Mn1—O3i—C4i	−14.73 (10)	C1—C2—C3—Cl1	−179.11 (13)
O3i—Mn1—O2—C2	86.98 (10)	C1—C2—C3—C1ii	3.8 (3)
O2i—Mn1—O3—C4	14.73 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1iii	0.76 (4)	2.07 (3)	2.8200 (17)	167 (4)

Table 1

Selected bond lengths (Å)

Mn1—O1	2.1884 (13)
Mn1—O2	2.1491 (11)
Mn1—O3	2.2042 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O1i	0.76 (4)	2.07 (3)	2.8200 (17)	167 (4)

Symmetry code: (i) .