trans-Diaqua-bis[5-carb-oxy-2-(3-pyridyl)-1H-imidazole-4-carboxyl-ato-κN,O]manganese(II).

In the title compound, [Mn(C(10)H(6)N(3)O(4))(2)(H(2)O)(2)], synthesized by hydro-thermal reaction, the Mn(II) ion lies on an inversion centre and displays a distorted octa-hedral coordination geometry defined by the two imidazole N atoms and two carboxylate O atoms of the two trans-standing chelate ligands, and two O atoms of the water mol-ecules. A two-dimensional supra-molecular architecture is formed via N-H⋯O, O-H⋯N and O-H⋯O hydrogen-bonding inter-actions.

Related literature

For the chemistry of imidazoles, see: Xiao et al. (2004 ▶); Zhang et al. (2004 ▶); Lu et al. (2006 ▶).

Experimental

Crystal data

[Mn(C10H6N3O4)2(H2O)2]

M = 555.33

Triclinic,

a = 6.9574 (7) Å

b = 8.5636 (7) Å

c = 9.4409 (16) Å

α = 81.90 (3)°

β = 83.42 (4)°

γ = 72.10 (2)°

V = 528.41 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.70 mm−1

T = 298 (2) K

0.25 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.845, T max = 0.869

5416 measured reflections

2378 independent reflections

1871 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.165

S = 1.11

2378 reflections

175 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029073/bx2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029073/bx2177Isup2.hkl

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

[Mn(C10H6N3O4)2(H2O)2]	Z = 1
Mr = 555.33	F(000) = 283
Triclinic, P1	Dx = 1.745 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9574 (7) Å	Cell parameters from 1463 reflections
b = 8.5636 (7) Å	θ = 3.1–27.5°
c = 9.4409 (16) Å	µ = 0.70 mm−1
α = 81.90 (3)°	T = 298 K
β = 83.42 (4)°	Block, colourless
γ = 72.10 (2)°	0.25 × 0.20 × 0.20 mm
V = 528.41 (11) Å3

Rigaku Mercury2 diffractometer	2378 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.845, Tmax = 0.869	l = −12→12
5416 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.1003P)2 + 0.0122P] where P = (Fo2 + 2Fc2)/3
2378 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.54 e Å−3
2 restraints	Δρmin = −0.44 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	0.5000	0.5000	0.0000	0.0299 (2)
C1	0.3266 (4)	0.8677 (4)	−0.0160 (3)	0.0290 (6)
C2	0.2634 (4)	0.8148 (3)	0.1332 (3)	0.0253 (6)
C3	0.1577 (4)	0.9082 (3)	0.2405 (3)	0.0260 (6)
C4	0.0487 (5)	1.0861 (4)	0.2425 (3)	0.0308 (6)
C5	0.2472 (4)	0.6428 (3)	0.3206 (3)	0.0229 (5)
C6	0.2698 (4)	0.4926 (3)	0.4203 (3)	0.0253 (6)
C7	0.3049 (5)	0.3401 (4)	0.3713 (3)	0.0336 (7)
H7A	0.3120	0.3314	0.2737	0.040*
C8	0.3291 (5)	0.2013 (4)	0.4703 (3)	0.0369 (7)
H8A	0.3592	0.0972	0.4399	0.044*
C9	0.3080 (5)	0.2195 (4)	0.6156 (3)	0.0345 (7)
H9A	0.3215	0.1261	0.6817	0.041*
N3	0.2692 (4)	0.3661 (3)	0.6640 (3)	0.0332 (6)
C11	0.2491 (5)	0.4986 (4)	0.5688 (3)	0.0300 (6)
H11A	0.2196	0.6010	0.6025	0.036*
N1	0.3172 (3)	0.6504 (3)	0.1834 (2)	0.0255 (5)
N2	0.1531 (4)	0.7971 (3)	0.3573 (2)	0.0269 (5)
H2A	0.0992	0.8207	0.4412	0.032*
O1	0.4330 (4)	0.7595 (3)	−0.0912 (2)	0.0380 (5)
O2	0.2722 (4)	1.0220 (3)	−0.0599 (2)	0.0408 (6)
O3	0.0641 (4)	1.1816 (3)	0.1292 (2)	0.0397 (6)
H3	0.1602	1.1348	0.0764	0.060*
O4	−0.0526 (4)	1.1310 (3)	0.3540 (2)	0.0457 (6)
O5	0.7793 (4)	0.5087 (3)	0.0738 (2)	0.0414 (6)
H5	0.7544	0.5539	0.1476	0.062*
H5B	0.867 (5)	0.416 (3)	0.083 (3)	0.042 (10)*

	U11	U22	U33	U12	U13	U23
Mn1	0.0369 (4)	0.0247 (4)	0.0204 (3)	0.0026 (3)	0.0007 (3)	−0.0056 (2)
C1	0.0337 (15)	0.0254 (14)	0.0204 (13)	0.0004 (11)	0.0015 (11)	−0.0017 (10)
C2	0.0307 (14)	0.0207 (13)	0.0197 (13)	−0.0006 (10)	−0.0005 (11)	−0.0035 (10)
C3	0.0315 (14)	0.0231 (14)	0.0205 (12)	−0.0040 (11)	0.0015 (11)	−0.0049 (10)
C4	0.0366 (16)	0.0242 (14)	0.0257 (14)	0.0005 (12)	−0.0005 (12)	−0.0061 (11)
C5	0.0233 (13)	0.0235 (13)	0.0184 (12)	−0.0021 (10)	0.0020 (10)	−0.0047 (9)
C6	0.0270 (13)	0.0265 (14)	0.0208 (13)	−0.0063 (11)	0.0028 (11)	−0.0041 (10)
C7	0.0455 (17)	0.0288 (15)	0.0212 (14)	−0.0052 (13)	0.0077 (13)	−0.0064 (11)
C8	0.0493 (19)	0.0225 (14)	0.0336 (16)	−0.0033 (12)	−0.0003 (14)	−0.0048 (11)
C9	0.0404 (17)	0.0279 (15)	0.0303 (16)	−0.0074 (13)	0.0003 (13)	0.0039 (12)
N3	0.0419 (15)	0.0327 (13)	0.0209 (12)	−0.0075 (11)	0.0023 (10)	−0.0012 (9)
C11	0.0388 (16)	0.0271 (14)	0.0226 (14)	−0.0065 (12)	−0.0030 (12)	−0.0041 (11)
N1	0.0310 (12)	0.0214 (11)	0.0200 (11)	−0.0021 (9)	−0.0007 (10)	−0.0028 (9)
N2	0.0334 (12)	0.0246 (12)	0.0185 (11)	−0.0032 (10)	0.0038 (9)	−0.0058 (8)
O1	0.0503 (14)	0.0304 (11)	0.0210 (10)	0.0023 (10)	0.0077 (9)	−0.0028 (8)
O2	0.0578 (14)	0.0251 (11)	0.0257 (11)	0.0011 (10)	0.0082 (10)	0.0035 (8)
O3	0.0508 (14)	0.0229 (11)	0.0330 (12)	0.0038 (9)	0.0059 (10)	−0.0031 (8)
O4	0.0650 (16)	0.0303 (12)	0.0291 (12)	0.0059 (11)	0.0040 (11)	−0.0123 (9)
O5	0.0423 (13)	0.0434 (14)	0.0309 (12)	0.0012 (11)	−0.0015 (10)	−0.0119 (10)

Mn1—O5i	2.163 (2)	C5—N2	1.356 (3)
Mn1—O5	2.163 (2)	C5—C6	1.460 (4)
Mn1—O1i	2.194 (2)	C6—C7	1.389 (4)
Mn1—O1	2.194 (2)	C6—C11	1.399 (4)
Mn1—N1i	2.322 (2)	C7—C8	1.383 (4)
Mn1—N1	2.322 (2)	C7—H7A	0.9300
C1—O1	1.246 (3)	C8—C9	1.388 (4)
C1—O2	1.279 (3)	C8—H8A	0.9300
C1—C2	1.477 (4)	C9—N3	1.335 (4)
C2—N1	1.370 (3)	C9—H9A	0.9300
C2—C3	1.380 (4)	N3—C11	1.326 (4)
C3—N2	1.355 (3)	C11—H11A	0.9300
C3—C4	1.480 (4)	N2—H2A	0.8600
C4—O4	1.238 (3)	O3—H3	0.8200
C4—O3	1.267 (4)	O5—H5	0.8200
C5—N1	1.331 (3)	O5—H5B	0.839 (17)
O5i—Mn1—O5	180.00 (11)	N2—C5—C6	123.9 (2)
O5i—Mn1—O1i	90.51 (10)	C7—C6—C11	117.7 (3)
O5—Mn1—O1i	89.49 (10)	C7—C6—C5	121.3 (2)
O5i—Mn1—O1	89.49 (10)	C11—C6—C5	121.0 (2)
O5—Mn1—O1	90.51 (10)	C8—C7—C6	118.9 (3)
O1i—Mn1—O1	180.0	C8—C7—H7A	120.6
O5i—Mn1—N1i	90.00 (8)	C6—C7—H7A	120.6
O5—Mn1—N1i	90.00 (8)	C7—C8—C9	119.2 (3)
O1i—Mn1—N1i	74.86 (8)	C7—C8—H8A	120.4
O1—Mn1—N1i	105.14 (8)	C9—C8—H8A	120.4
O5i—Mn1—N1	90.00 (8)	N3—C9—C8	122.5 (3)
O5—Mn1—N1	90.00 (8)	N3—C9—H9A	118.8
O1i—Mn1—N1	105.14 (8)	C8—C9—H9A	118.8
O1—Mn1—N1	74.86 (8)	C11—N3—C9	118.2 (3)
N1i—Mn1—N1	180.0	N3—C11—C6	123.5 (3)
O1—C1—O2	123.7 (3)	N3—C11—H11A	118.2
O1—C1—C2	118.1 (3)	C6—C11—H11A	118.2
O2—C1—C2	118.2 (3)	C5—N1—C2	105.7 (2)
N1—C2—C3	110.3 (2)	C5—N1—Mn1	145.47 (18)
N1—C2—C1	119.8 (2)	C2—N1—Mn1	108.75 (16)
C3—C2—C1	129.9 (3)	C3—N2—C5	109.1 (2)
N2—C3—C2	104.8 (2)	C3—N2—H2A	125.5
N2—C3—C4	121.9 (2)	C5—N2—H2A	125.5
C2—C3—C4	133.1 (3)	C1—O1—Mn1	118.36 (18)
O4—C4—O3	124.5 (3)	C4—O3—H3	109.5
O4—C4—C3	117.8 (3)	Mn1—O5—H5	109.5
O3—C4—C3	117.7 (2)	Mn1—O5—H5B	113 (2)
N1—C5—N2	110.0 (2)	H5—O5—H5B	112.4
N1—C5—C6	126.0 (2)
O1—C1—C2—N1	−1.9 (4)	C6—C5—N1—C2	−179.2 (3)
O2—C1—C2—N1	179.4 (3)	N2—C5—N1—Mn1	176.6 (2)
O1—C1—C2—C3	175.6 (3)	C6—C5—N1—Mn1	−2.2 (5)
O2—C1—C2—C3	−3.1 (5)	C3—C2—N1—C5	−0.6 (3)
N1—C2—C3—N2	1.4 (3)	C1—C2—N1—C5	177.3 (3)
C1—C2—C3—N2	−176.2 (3)	C3—C2—N1—Mn1	−178.84 (19)
N1—C2—C3—C4	−173.1 (3)	C1—C2—N1—Mn1	−0.9 (3)
C1—C2—C3—C4	9.3 (6)	O5i—Mn1—N1—C5	95.6 (3)
N2—C3—C4—O4	−1.9 (5)	O5—Mn1—N1—C5	−84.4 (3)
C2—C3—C4—O4	171.9 (3)	O1i—Mn1—N1—C5	5.0 (4)
N2—C3—C4—O3	178.8 (3)	O1—Mn1—N1—C5	−175.0 (4)
C2—C3—C4—O3	−7.4 (5)	O5i—Mn1—N1—C2	−87.49 (19)
N1—C5—C6—C7	−22.7 (4)	O5—Mn1—N1—C2	92.51 (19)
N2—C5—C6—C7	158.6 (3)	O1i—Mn1—N1—C2	−178.01 (18)
N1—C5—C6—C11	159.7 (3)	O1—Mn1—N1—C2	1.99 (18)
N2—C5—C6—C11	−18.9 (4)	C2—C3—N2—C5	−1.7 (3)
C11—C6—C7—C8	−3.7 (4)	C4—C3—N2—C5	173.6 (3)
C5—C6—C7—C8	178.7 (3)	N1—C5—N2—C3	1.4 (3)
C6—C7—C8—C9	3.1 (5)	C6—C5—N2—C3	−179.8 (2)
C7—C8—C9—N3	−1.4 (5)	O2—C1—O1—Mn1	−177.4 (2)
C8—C9—N3—C11	0.4 (5)	C2—C1—O1—Mn1	3.9 (4)
C9—N3—C11—C6	−1.1 (5)	O5i—Mn1—O1—C1	86.8 (2)
C7—C6—C11—N3	2.8 (4)	O5—Mn1—O1—C1	−93.2 (2)
C5—C6—C11—N3	−179.6 (3)	N1i—Mn1—O1—C1	176.7 (2)
N2—C5—N1—C2	−0.4 (3)	N1—Mn1—O1—C1	−3.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ii	0.86	2.00	2.840 (3)	164.
O5—H5···N3iii	0.82	1.97	2.779 (3)	171.
O5—H5B···O3iv	0.84 (2)	2.07 (2)	2.908 (3)	173 (3)
O3—H3···O2	0.82	1.69	2.456 (3)	155.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.86	2.00	2.840 (3)	164
O5—H5⋯N3ii	0.82	1.97	2.779 (3)	171
O5—H5B⋯O3iii	0.839 (17)	2.074 (18)	2.908 (3)	173 (3)
O3—H3⋯O2	0.82	1.69	2.456 (3)	155

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