Diaqua-bis-(1H-imidazole-4-carboxyl-ato-κ(2) N (3),O (4))manganese(II).

In the title compound, [Mn(C4H3N2O2)2(H2O)2], the Mn(II) ion is located on a twofold rotation axis and displays a distorted octa-hedral coordination environment, defined by two N,O-bidentate 1H-imidazole-4-carboxyl-ate ligands in the equatorial plane and two water mol-ecules in axial positions. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional supra-molecular network. π-π stacking inter-actions between the imidazole rings [centroid-centroid distances = 3.5188 (15) and 3.6687 (15) Å] further stabilize the structure.

Related literature

For related structures, see: Cai et al. (2012 ▶); Chen (2012 ▶); Gryz et al. (2007 ▶); Haggag (2005 ▶); Shuai et al. (2011 ▶); Starosta & Leciejewicz (2006 ▶); Yin et al. (2009 ▶); Zheng et al. (2011 ▶).

Experimental

Crystal data

[Mn(C4H3N2O2)2(H2O)2]

M = 313.14

Orthorhombic,

a = 7.3052 (10) Å

b = 11.7997 (17) Å

c = 13.5156 (19) Å

V = 1165.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 298 K

0.36 × 0.32 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.679, T max = 0.721

5775 measured reflections

1145 independent reflections

972 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.07

1145 reflections

87 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004091/hy2616sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004091/hy2616Isup2.hkl

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

[Mn(C4H3N2O2)2(H2O)2]	F(000) = 636
Mr = 313.14	Dx = 1.785 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1516 reflections
a = 7.3052 (10) Å	θ = 3.3–24.9°
b = 11.7997 (17) Å	µ = 1.16 mm−1
c = 13.5156 (19) Å	T = 298 K
V = 1165.0 (3) Å3	Block, colourless
Z = 4	0.36 × 0.32 × 0.30 mm

Bruker APEXII CCD diffractometer	1145 independent reflections
Radiation source: fine-focus sealed tube	972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
φ and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.679, Tmax = 0.721	k = −14→10
5775 measured reflections	l = −16→15

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) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.3284P] where P = (Fo2 + 2Fc2)/3
1145 reflections	(Δ/σ)max = 0.001
87 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.57 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	0.7500	0.7500	0.63202 (3)	0.0256 (2)
N1	0.5501 (2)	0.81048 (17)	0.52125 (14)	0.0282 (5)
N2	0.3599 (3)	0.87066 (19)	0.40742 (14)	0.0342 (5)
H2	0.3136	0.8835	0.3500	0.041*
C1	0.4022 (3)	0.87462 (18)	0.67505 (16)	0.0238 (5)
C2	0.4063 (3)	0.86601 (18)	0.56583 (16)	0.0241 (5)
C4	0.5155 (3)	0.8144 (2)	0.42597 (17)	0.0350 (6)
H4	0.5895	0.7822	0.3775	0.042*
C3	0.2882 (4)	0.9039 (2)	0.49557 (18)	0.0312 (5)
H3	0.1804	0.9442	0.5057	0.037*
O1	0.5374 (2)	0.83532 (14)	0.72111 (11)	0.0310 (4)
O2	0.2642 (2)	0.91985 (15)	0.71532 (12)	0.0302 (4)
O1W	0.5981 (2)	0.59207 (14)	0.66084 (14)	0.0392 (5)
H1WA	0.6528	0.5466	0.7024	0.059*
H1WB	0.5022	0.5856	0.6758	0.059*

	U11	U22	U33	U12	U13	U23
Mn1	0.0235 (4)	0.0344 (4)	0.0189 (3)	0.00646 (18)	0.000	0.000
N1	0.0272 (11)	0.0389 (12)	0.0184 (10)	0.0068 (8)	−0.0009 (8)	−0.0021 (8)
N2	0.0348 (13)	0.0490 (13)	0.0186 (10)	0.0037 (9)	−0.0074 (8)	0.0014 (8)
C1	0.0247 (12)	0.0233 (11)	0.0233 (12)	−0.0029 (9)	0.0020 (9)	−0.0011 (8)
C2	0.0243 (12)	0.0288 (12)	0.0192 (12)	0.0008 (9)	0.0002 (9)	−0.0007 (8)
C4	0.0359 (15)	0.0506 (16)	0.0186 (12)	0.0067 (11)	0.0000 (10)	−0.0031 (10)
C3	0.0289 (12)	0.0391 (13)	0.0256 (13)	0.0037 (10)	−0.0008 (10)	0.0009 (10)
O1	0.0287 (10)	0.0457 (10)	0.0186 (8)	0.0087 (7)	−0.0010 (7)	−0.0002 (7)
O2	0.0243 (10)	0.0432 (11)	0.0232 (10)	0.0047 (6)	0.0048 (6)	−0.0051 (7)
O1W	0.0279 (10)	0.0429 (11)	0.0467 (12)	0.0036 (7)	0.0039 (8)	0.0133 (8)

Mn1—O1W	2.2037 (17)	N2—H2	0.8600
Mn1—O1Wi	2.2038 (17)	C1—O1	1.257 (3)
Mn1—O1i	2.2079 (16)	C1—O2	1.264 (3)
Mn1—O1	2.2079 (16)	C1—C2	1.480 (3)
Mn1—N1	2.2097 (19)	C2—C3	1.359 (3)
Mn1—N1i	2.2097 (19)	C4—H4	0.9300
N1—C4	1.313 (3)	C3—H3	0.9300
N1—C2	1.377 (3)	O1W—H1WA	0.87
N2—C4	1.340 (3)	O1W—H1WB	0.73
N2—C3	1.359 (3)
O1W—Mn1—O1Wi	159.64 (10)	C4—N2—H2	126.1
O1W—Mn1—O1i	82.66 (6)	C3—N2—H2	126.1
O1Wi—Mn1—O1i	86.27 (6)	O1—C1—O2	124.7 (2)
O1W—Mn1—O1	86.27 (6)	O1—C1—C2	116.93 (18)
O1Wi—Mn1—O1	82.66 (6)	O2—C1—C2	118.34 (19)
O1i—Mn1—O1	113.90 (8)	C3—C2—N1	109.6 (2)
O1W—Mn1—N1	93.44 (7)	C3—C2—C1	131.4 (2)
O1Wi—Mn1—N1	100.34 (7)	N1—C2—C1	118.98 (18)
O1i—Mn1—N1	168.96 (6)	N1—C4—N2	111.4 (2)
O1—Mn1—N1	75.97 (7)	N1—C4—H4	124.3
O1W—Mn1—N1i	100.34 (7)	N2—C4—H4	124.3
O1Wi—Mn1—N1i	93.44 (7)	C2—C3—N2	105.9 (2)
O1i—Mn1—N1i	75.96 (7)	C2—C3—H3	127.1
O1—Mn1—N1i	168.97 (6)	N2—C3—H3	127.1
N1—Mn1—N1i	94.70 (10)	C1—O1—Mn1	116.82 (14)
C4—N1—C2	105.38 (19)	Mn1—O1W—H1WA	113.7
C4—N1—Mn1	143.43 (17)	Mn1—O1W—H1WB	128.2
C2—N1—Mn1	111.19 (14)	H1WA—O1W—H1WB	101.3
C4—N2—C3	107.8 (2)
O1W—Mn1—N1—C4	−95.6 (3)	O1—C1—C2—N1	3.7 (3)
O1Wi—Mn1—N1—C4	99.5 (3)	O2—C1—C2—N1	−175.9 (2)
O1i—Mn1—N1—C4	−26.7 (5)	C2—N1—C4—N2	1.0 (3)
O1—Mn1—N1—C4	179.1 (3)	Mn1—N1—C4—N2	−178.4 (2)
N1i—Mn1—N1—C4	5.1 (3)	C3—N2—C4—N1	−0.8 (3)
O1W—Mn1—N1—C2	85.01 (16)	N1—C2—C3—N2	0.3 (3)
O1Wi—Mn1—N1—C2	−79.94 (16)	C1—C2—C3—N2	−179.3 (2)
O1i—Mn1—N1—C2	153.9 (3)	C4—N2—C3—C2	0.3 (3)
O1—Mn1—N1—C2	−0.28 (15)	O2—C1—O1—Mn1	175.69 (16)
N1i—Mn1—N1—C2	−174.31 (19)	C2—C1—O1—Mn1	−3.9 (2)
C4—N1—C2—C3	−0.8 (3)	O1W—Mn1—O1—C1	−92.12 (16)
Mn1—N1—C2—C3	178.83 (16)	O1Wi—Mn1—O1—C1	105.01 (16)
C4—N1—C2—C1	178.8 (2)	O1i—Mn1—O1—C1	−172.39 (18)
Mn1—N1—C2—C1	−1.5 (2)	N1—Mn1—O1—C1	2.38 (16)
O1—C1—C2—C3	−176.7 (2)	N1i—Mn1—O1—C1	35.2 (4)
O2—C1—C2—C3	3.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ii	0.86	1.95	2.811 (3)	173
O1W—H1WA···O2iii	0.87	1.96	2.818 (2)	167
O1W—H1WB···O2iv	0.73	2.02	2.751 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	1.95	2.811 (3)	173
O1W—H1WA⋯O2ii	0.87	1.96	2.818 (2)	167
O1W—H1WB⋯O2iii	0.73	2.02	2.751 (2)	176

Symmetry codes: (i) ; (ii) ; (iii) .