Diaqua-bis(5-carb-oxy-2-methyl-1H-imidazole-4-carboxyl-ato-κN,O)manganese(II).

The title complex, [Mn(C(6)H(5)N(2)O(4))(2)(H(2)O)(2)], was obtained by hydro-thermal synthesis. The Mn(II) atom, which lies on an inversion centre, displays a slightly distorted octa-hedral geometry. In the crystal packing, complex mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds to form a three-dimensional supramolecular structure. The title complex is isostructural with the corresponding cadmium(II) complex [Nie, Wen, Wu, Liu & Liu (2007 ▶). Acta Cryst. E63, m753-m755].

Related literature

For related literature, see: Liang et al. (2002 ▶); Net et al. (1989 ▶); Nie et al. (2007 ▶); Ying & Mao (2006 ▶).

Experimental

Crystal data

[Mn(C6H5N2O4)2(H2O)2]

M = 429.21

Monoclinic,

a = 12.2047 (12) Å

b = 9.1607 (9) Å

c = 7.3860 (7) Å

β = 101.355 (2)°

V = 809.62 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.88 mm−1

T = 293 (2) K

0.30 × 0.21 × 0.12 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.778, T max = 0.902

5936 measured reflections

1931 independent reflections

1387 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 0.96

1931 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800411X/rz2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800411X/rz2194Isup2.hkl

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

[Mn(C6H5N2O4)2(H2O)2]	F000 = 438
Mr = 429.21	Dx = 1.761 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3147 reflections
a = 12.2047 (12) Å	θ = 2.8–28.2º
b = 9.1607 (9) Å	µ = 0.88 mm−1
c = 7.3860 (7) Å	T = 293 (2) K
β = 101.355 (2)º	Plate, colourless
V = 809.62 (14) Å3	0.30 × 0.21 × 0.12 mm
Z = 2

Bruker APEX area-detector diffractometer	1931 independent reflections
Radiation source: fine-focus sealed tube	1387 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 293(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	h = −16→16
Tmin = 0.778, Tmax = 0.902	k = −12→12
5936 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
1931 reflections	Δρmax = 0.35 e Å−3
132 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.0000	0.5000	0.0000	0.02937 (16)
N1	0.18504 (13)	0.50974 (16)	0.1269 (2)	0.0293 (4)
N2	0.35369 (14)	0.52117 (17)	0.2952 (3)	0.0363 (4)
H2A	0.4143	0.5577	0.3581	0.044*
O1	0.50357 (12)	0.30235 (19)	0.4426 (3)	0.0559 (5)
O2	0.39335 (12)	0.12886 (16)	0.3029 (2)	0.0484 (4)
H2B	0.3298	0.1226	0.2415	0.073*
O3	0.19549 (11)	0.11771 (14)	0.1132 (2)	0.0352 (4)
O4	0.06082 (11)	0.27347 (14)	−0.01036 (19)	0.0330 (3)
O5	−0.02904 (16)	0.4590 (2)	0.2723 (3)	0.0459 (5)
C1	0.2586 (2)	0.7599 (2)	0.2185 (4)	0.0549 (7)
H1A	0.1875	0.7922	0.1503	0.082*
H1B	0.3172	0.8005	0.1645	0.082*
H1C	0.2675	0.7915	0.3444	0.082*
C2	0.26397 (16)	0.5981 (2)	0.2124 (3)	0.0339 (5)
C3	0.41682 (17)	0.2662 (2)	0.3431 (3)	0.0370 (5)
C4	0.33359 (15)	0.3766 (2)	0.2638 (3)	0.0309 (5)
C5	0.22732 (15)	0.3710 (2)	0.1569 (3)	0.0273 (4)
C6	0.15691 (15)	0.2449 (2)	0.0818 (3)	0.0277 (4)
H5B	−0.071 (2)	0.499 (2)	0.319 (4)	0.041 (8)*
H5A	0.001 (2)	0.397 (3)	0.336 (4)	0.065 (9)*

	U11	U22	U33	U12	U13	U23
Mn1	0.0254 (2)	0.0274 (2)	0.0312 (3)	0.00137 (17)	−0.00438 (17)	0.00092 (17)
N1	0.0265 (9)	0.0253 (8)	0.0328 (10)	−0.0015 (6)	−0.0023 (7)	−0.0002 (7)
N2	0.0232 (8)	0.0327 (10)	0.0468 (12)	−0.0040 (7)	−0.0081 (7)	−0.0053 (8)
O1	0.0338 (9)	0.0507 (10)	0.0697 (12)	0.0059 (7)	−0.0231 (8)	−0.0116 (9)
O2	0.0350 (8)	0.0358 (9)	0.0650 (11)	0.0064 (7)	−0.0127 (7)	−0.0026 (7)
O3	0.0305 (7)	0.0248 (7)	0.0466 (9)	−0.0008 (6)	−0.0011 (6)	−0.0008 (6)
O4	0.0275 (7)	0.0276 (7)	0.0379 (9)	−0.0018 (6)	−0.0080 (6)	−0.0034 (6)
O5	0.0493 (11)	0.0499 (10)	0.0391 (10)	0.0240 (9)	0.0099 (8)	0.0137 (8)
C1	0.0500 (15)	0.0375 (13)	0.071 (2)	0.0001 (11)	−0.0042 (13)	−0.0063 (12)
C2	0.0283 (10)	0.0309 (10)	0.0388 (13)	−0.0037 (8)	−0.0029 (9)	−0.0022 (9)
C3	0.0276 (10)	0.0376 (12)	0.0415 (14)	0.0043 (8)	−0.0037 (9)	−0.0016 (10)
C4	0.0244 (10)	0.0317 (11)	0.0335 (12)	−0.0012 (8)	−0.0022 (8)	−0.0025 (8)
C5	0.0230 (9)	0.0293 (10)	0.0275 (11)	−0.0010 (7)	−0.0003 (7)	−0.0006 (8)
C6	0.0255 (10)	0.0276 (10)	0.0286 (11)	−0.0023 (8)	0.0015 (8)	−0.0010 (8)

Mn1—O5i	2.1433 (19)	O2—H2B	0.8200
Mn1—O5	2.1433 (19)	O3—C6	1.261 (2)
Mn1—O4	2.2103 (13)	O4—C6	1.262 (2)
Mn1—O4i	2.2103 (13)	O5—H5B	0.77 (3)
Mn1—N1	2.2700 (16)	O5—H5A	0.78 (3)
Mn1—N1i	2.2700 (16)	C1—C2	1.485 (3)
N1—C2	1.320 (2)	C1—H1A	0.9600
N1—C5	1.373 (2)	C1—H1B	0.9600
N2—C2	1.344 (3)	C1—H1C	0.9600
N2—C4	1.358 (2)	C3—C4	1.471 (3)
N2—H2A	0.8600	C4—C5	1.380 (3)
O1—C3	1.210 (2)	C5—C6	1.481 (3)
O2—C3	1.311 (2)
O5i—Mn1—O5	180.00 (10)	Mn1—O5—H5A	124 (2)
O5i—Mn1—O4	90.77 (6)	H5B—O5—H5A	110 (3)
O5—Mn1—O4	89.23 (6)	C2—C1—H1A	109.5
O5i—Mn1—O4i	89.23 (6)	C2—C1—H1B	109.5
O5—Mn1—O4i	90.77 (6)	H1A—C1—H1B	109.5
O4—Mn1—O4i	180.00 (10)	C2—C1—H1C	109.5
O5i—Mn1—N1	92.62 (7)	H1A—C1—H1C	109.5
O5—Mn1—N1	87.38 (7)	H1B—C1—H1C	109.5
O4—Mn1—N1	74.79 (5)	N1—C2—N2	110.42 (18)
O4i—Mn1—N1	105.21 (5)	N1—C2—C1	126.44 (19)
O5i—Mn1—N1i	87.38 (7)	N2—C2—C1	123.14 (18)
O5—Mn1—N1i	92.62 (7)	O1—C3—O2	121.74 (19)
O4—Mn1—N1i	105.21 (5)	O1—C3—C4	120.44 (19)
O4i—Mn1—N1i	74.79 (5)	O2—C3—C4	117.82 (17)
N1—Mn1—N1i	180.00 (8)	N2—C4—C5	104.59 (16)
C2—N1—C5	105.93 (16)	N2—C4—C3	121.00 (17)
C2—N1—Mn1	142.63 (14)	C5—C4—C3	134.39 (18)
C5—N1—Mn1	110.00 (11)	N1—C5—C4	109.80 (15)
C2—N2—C4	109.25 (16)	N1—C5—C6	119.32 (16)
C2—N2—H2A	125.4	C4—C5—C6	130.84 (17)
C4—N2—H2A	125.4	O4—C6—O3	124.39 (16)
C3—O2—H2B	109.5	O4—C6—C5	116.68 (16)
C6—O4—Mn1	117.32 (11)	O3—C6—C5	118.93 (16)
Mn1—O5—H5B	126 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O3ii	0.77 (3)	2.01 (3)	2.763 (2)	168 (3)
O5—H5A···O4iii	0.78 (3)	1.98 (3)	2.760 (2)	174 (3)
N2—H2A···O1iv	0.86	2.06	2.841 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O3i	0.77 (3)	2.01 (3)	2.763 (2)	168 (3)
O5—H5A⋯O4ii	0.78 (3)	1.98 (3)	2.760 (2)	174 (3)
N2—H2A⋯O1iii	0.86	2.06	2.841 (2)	151

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