Diaqua-bis{5-carboxy-2-[(1H-1,2,4-triazol-1-yl)-meth-yl]-1H-imidazole-4-carboxyl-ato}-manganese(II).

In the title compound, [Mn(C(8)H(6)N(5)O(4))(2)(H(2)O)(2)], the Mn(II) ion is situated on an inversion center and is six-coordinated by two N and two O atoms from two L ligands (HL = 2-[(1H-1,2,4-triazol-1-yl)meth-yl]-1H-imidazole-4,5-dicarboxylic acid) and two water mol-ecules in a distorted octa-hedral geometry. In ligand L, the imidazole and triazole rings form a dihedral angle of 74.25 (8)°. Mol-ecules are assembled into a three-dimensional structure via inter-molecular O-H⋯O, O-H⋯N and N-H⋯N hydrogen-bonds, and π-π inter-actions with a short distance of 3.665 (2) Å between the centroids of the imidazole and triazole rings of neighbouring mol-ecules.

Related literature

For related structures, see: Lee et al. (2005 ▶); Ouellette et al. (2007 ▶); Won et al. (2007 ▶).

Experimental

Crystal data

[Mn(C8H6N5O4)2(H2O)2]

M = 563.33

Monoclinic,

a = 7.730 (2) Å

b = 14.498 (3) Å

c = 11.588 (4) Å

β = 125.70 (2)°

V = 1054.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.71 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.871, T max = 0.933

11281 measured reflections

2074 independent reflections

1974 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.077

S = 1.05

2074 reflections

169 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); 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 global, I. DOI: 10.1107/S1600536810012626/cv2709sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012626/cv2709Isup2.hkl

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

[Mn(C8H6N5O4)2(H2O)2]	F(000) = 574
Mr = 563.33	Dx = 1.774 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3276 reflections
a = 7.730 (2) Å	θ = 2.6–30.8°
b = 14.498 (3) Å	µ = 0.71 mm−1
c = 11.588 (4) Å	T = 293 K
β = 125.70 (2)°	Prism, pink
V = 1054.6 (5) Å3	0.20 × 0.15 × 0.10 mm
Z = 2

Rigaku Mercury CCD area-detector diffractometer	2074 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −9→9
Tmin = 0.871, Tmax = 0.933	k = −17→17
11281 measured reflections	l = −13→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0245P)2 + 0.947P] where P = (Fo2 + 2Fc2)/3
2074 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles.

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	0.0000	0.0000	0.02963 (14)
O1	−0.2806 (2)	0.11091 (10)	0.13249 (15)	0.0333 (4)
O2	−0.0902 (2)	0.17418 (10)	0.34848 (15)	0.0319 (3)
O3	−0.0253 (2)	0.14770 (10)	0.58250 (15)	0.0328 (4)
H3C	−0.0491	0.1596	0.4908	0.049*
O4	−0.1284 (2)	0.04886 (11)	0.67687 (15)	0.0353 (4)
O5	−0.7693 (3)	0.08739 (13)	−0.05545 (17)	0.0516 (5)
H5B	−0.7549	0.1335	−0.0155	0.077*
H5C	−0.8757	0.0886	−0.1346	0.077*
N1	−0.4778 (3)	−0.24271 (11)	0.21460 (17)	0.0247 (4)
N2	−0.3256 (3)	−0.29594 (12)	0.32424 (18)	0.0316 (4)
N3	−0.3707 (3)	−0.33526 (13)	0.12013 (18)	0.0318 (4)
N4	−0.4235 (3)	−0.02708 (11)	0.21633 (16)	0.0229 (4)
N5	−0.3572 (3)	−0.05521 (11)	0.42541 (16)	0.0221 (4)
H5A	−0.3594	−0.0820	0.4907	0.026*
C1	−0.2671 (4)	−0.34974 (16)	0.2612 (2)	0.0337 (5)
H1A	−0.1620	−0.3945	0.3101	0.040*
C2	−0.5007 (4)	−0.26688 (14)	0.0956 (2)	0.0290 (5)
H2A	−0.5952	−0.2394	0.0074	0.035*
C3	−0.5880 (3)	−0.16935 (14)	0.2336 (2)	0.0283 (5)
H3A	−0.6208	−0.1902	0.2984	0.034*
H3B	−0.7215	−0.1559	0.1430	0.034*
C4	−0.4575 (3)	−0.08370 (13)	0.2908 (2)	0.0219 (4)
C5	−0.2913 (3)	0.04042 (13)	0.30983 (19)	0.0208 (4)
C6	−0.2149 (3)	0.11379 (14)	0.2602 (2)	0.0249 (4)
C7	−0.2507 (3)	0.02413 (13)	0.44029 (19)	0.0212 (4)
C8	−0.1284 (3)	0.07527 (14)	0.5765 (2)	0.0252 (4)

	U11	U22	U33	U12	U13	U23
Mn1	0.0324 (3)	0.0372 (3)	0.0167 (2)	−0.0015 (2)	0.0129 (2)	0.00040 (18)
O1	0.0379 (9)	0.0365 (9)	0.0233 (8)	−0.0041 (7)	0.0166 (7)	0.0066 (6)
O2	0.0335 (8)	0.0273 (8)	0.0316 (8)	−0.0063 (6)	0.0172 (7)	−0.0006 (6)
O3	0.0347 (8)	0.0307 (8)	0.0279 (8)	−0.0076 (7)	0.0153 (7)	−0.0074 (6)
O4	0.0384 (9)	0.0452 (10)	0.0207 (8)	−0.0050 (7)	0.0162 (7)	−0.0059 (7)
O5	0.0416 (10)	0.0684 (13)	0.0262 (9)	0.0132 (9)	0.0093 (8)	−0.0137 (8)
N1	0.0317 (9)	0.0216 (9)	0.0235 (9)	−0.0040 (7)	0.0176 (8)	−0.0033 (7)
N2	0.0376 (10)	0.0316 (10)	0.0224 (9)	−0.0003 (8)	0.0156 (8)	0.0009 (7)
N3	0.0410 (11)	0.0312 (10)	0.0293 (10)	−0.0014 (8)	0.0240 (9)	−0.0032 (8)
N4	0.0250 (8)	0.0240 (9)	0.0175 (8)	−0.0010 (7)	0.0111 (7)	−0.0016 (6)
N5	0.0268 (9)	0.0229 (9)	0.0185 (8)	0.0000 (7)	0.0144 (7)	0.0004 (6)
C1	0.0351 (12)	0.0332 (12)	0.0300 (12)	0.0032 (10)	0.0174 (10)	0.0006 (9)
C2	0.0410 (12)	0.0249 (11)	0.0227 (10)	−0.0040 (9)	0.0196 (10)	−0.0022 (8)
C3	0.0330 (11)	0.0243 (11)	0.0332 (11)	−0.0039 (9)	0.0225 (10)	−0.0057 (9)
C4	0.0230 (10)	0.0213 (10)	0.0217 (10)	0.0002 (8)	0.0133 (8)	−0.0016 (8)
C5	0.0210 (9)	0.0201 (9)	0.0189 (9)	0.0021 (8)	0.0102 (8)	0.0004 (8)
C6	0.0234 (10)	0.0238 (10)	0.0240 (10)	0.0033 (8)	0.0119 (9)	0.0046 (8)
C7	0.0207 (9)	0.0214 (10)	0.0188 (9)	0.0019 (8)	0.0100 (8)	0.0004 (7)
C8	0.0227 (10)	0.0274 (11)	0.0211 (10)	0.0034 (8)	0.0102 (8)	−0.0025 (8)

Mn1—O5i	2.1886 (17)	N2—C1	1.316 (3)
Mn1—O5	2.1886 (17)	N3—C2	1.319 (3)
Mn1—O1i	2.1862 (16)	N3—C1	1.353 (3)
Mn1—O1	2.1862 (16)	N4—C4	1.324 (2)
Mn1—N4	2.2489 (18)	N4—C5	1.373 (2)
Mn1—N4i	2.2489 (18)	N5—C4	1.339 (2)
O1—C6	1.254 (2)	N5—C7	1.366 (2)
O2—C6	1.262 (2)	N5—H5A	0.8600
O3—C8	1.296 (3)	C1—H1A	0.9300
O3—H3C	0.9817	C2—H2A	0.9300
O4—C8	1.224 (2)	C3—C4	1.489 (3)
O5—H5B	0.7826	C3—H3A	0.9700
O5—H5C	0.7987	C3—H3B	0.9700
N1—C2	1.331 (3)	C5—C7	1.373 (3)
N1—N2	1.360 (2)	C5—C6	1.486 (3)
N1—C3	1.458 (3)	C7—C8	1.481 (3)
O5i—Mn1—O5	180.00 (12)	C4—N5—H5A	126.2
O5i—Mn1—O1i	89.74 (7)	C7—N5—H5A	126.2
O5—Mn1—O1i	90.26 (7)	N2—C1—N3	115.2 (2)
O5i—Mn1—O1	90.26 (7)	N2—C1—H1A	122.4
O5—Mn1—O1	89.74 (7)	N3—C1—H1A	122.4
O1i—Mn1—O1	180.00 (10)	N3—C2—N1	110.49 (19)
O5i—Mn1—N4	89.15 (6)	N3—C2—H2A	124.8
O5—Mn1—N4	90.85 (6)	N1—C2—H2A	124.8
O1i—Mn1—N4	104.25 (6)	N1—C3—C4	111.81 (16)
O1—Mn1—N4	75.75 (6)	N1—C3—H3A	109.3
O5i—Mn1—N4i	90.85 (6)	C4—C3—H3A	109.3
O5—Mn1—N4i	89.15 (6)	N1—C3—H3B	109.3
O1i—Mn1—N4i	75.75 (6)	C4—C3—H3B	109.3
O1—Mn1—N4i	104.25 (6)	H3A—C3—H3B	107.9
N4—Mn1—N4i	180.00 (11)	N4—C4—N5	111.56 (17)
C6—O1—Mn1	117.87 (13)	N4—C4—C3	124.59 (17)
C8—O3—H3C	111.3	N5—C4—C3	123.85 (18)
Mn1—O5—H5B	122.5	N4—C5—C7	109.45 (17)
Mn1—O5—H5C	121.0	N4—C5—C6	119.06 (16)
H5B—O5—H5C	110.9	C7—C5—C6	131.47 (18)
C2—N1—N2	109.77 (17)	O1—C6—O2	124.89 (19)
C2—N1—C3	127.77 (18)	O1—C6—C5	117.01 (18)
N2—N1—C3	122.43 (16)	O2—C6—C5	118.10 (17)
C1—N2—N1	102.01 (17)	N5—C7—C5	105.79 (16)
C2—N3—C1	102.53 (18)	N5—C7—C8	121.25 (17)
C4—N4—C5	105.50 (15)	C5—C7—C8	132.93 (18)
C4—N4—Mn1	144.26 (13)	O4—C8—O3	122.92 (18)
C5—N4—Mn1	110.24 (12)	O4—C8—C7	120.16 (19)
C4—N5—C7	107.68 (16)	O3—C8—C7	116.91 (18)
O5i—Mn1—O1—C6	−90.63 (15)	C5—N4—C4—C3	−178.15 (18)
O5—Mn1—O1—C6	89.37 (15)	Mn1—N4—C4—C3	2.4 (4)
O1i—Mn1—O1—C6	178 (100)	C7—N5—C4—N4	−0.3 (2)
N4—Mn1—O1—C6	−1.57 (14)	C7—N5—C4—C3	178.78 (18)
N4i—Mn1—O1—C6	178.43 (14)	N1—C3—C4—N4	73.8 (2)
C2—N1—N2—C1	−0.1 (2)	N1—C3—C4—N5	−105.2 (2)
C3—N1—N2—C1	−178.39 (18)	C4—N4—C5—C7	−1.2 (2)
O5i—Mn1—N4—C4	−87.9 (2)	Mn1—N4—C5—C7	178.46 (12)
O5—Mn1—N4—C4	92.1 (2)	C4—N4—C5—C6	177.62 (17)
O1i—Mn1—N4—C4	1.6 (2)	Mn1—N4—C5—C6	−2.7 (2)
O1—Mn1—N4—C4	−178.4 (2)	Mn1—O1—C6—O2	−179.15 (15)
N4i—Mn1—N4—C4	171 (100)	Mn1—O1—C6—C5	0.6 (2)
O5i—Mn1—N4—C5	92.68 (13)	N4—C5—C6—O1	1.6 (3)
O5—Mn1—N4—C5	−87.32 (13)	C7—C5—C6—O1	−179.9 (2)
O1i—Mn1—N4—C5	−177.81 (12)	N4—C5—C6—O2	−178.64 (17)
O1—Mn1—N4—C5	2.19 (12)	C7—C5—C6—O2	−0.1 (3)
N4i—Mn1—N4—C5	−9(100)	C4—N5—C7—C5	−0.4 (2)
N1—N2—C1—N3	−0.3 (2)	C4—N5—C7—C8	177.95 (17)
C2—N3—C1—N2	0.6 (3)	N4—C5—C7—N5	1.0 (2)
C1—N3—C2—N1	−0.7 (2)	C6—C5—C7—N5	−177.59 (19)
N2—N1—C2—N3	0.6 (2)	N4—C5—C7—C8	−177.1 (2)
C3—N1—C2—N3	178.69 (18)	C6—C5—C7—C8	4.3 (4)
C2—N1—C3—C4	−97.8 (2)	N5—C7—C8—O4	−3.0 (3)
N2—N1—C3—C4	80.2 (2)	C5—C7—C8—O4	174.9 (2)
C5—N4—C4—N5	0.9 (2)	N5—C7—C8—O3	177.23 (17)
Mn1—N4—C4—N5	−178.52 (16)	C5—C7—C8—O3	−4.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3C···O2	0.98	1.50	2.483 (2)	178
O5—H5B···N2ii	0.78	2.18	2.878 (2)	149
O5—H5C···O4iii	0.80	1.98	2.755 (2)	162
N5—H5A···N3iv	0.86	1.96	2.811 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3C⋯O2	0.98	1.50	2.483 (2)	178
O5—H5B⋯N2i	0.78	2.18	2.878 (2)	149
O5—H5C⋯O4ii	0.80	1.98	2.755 (2)	162
N5—H5A⋯N3iii	0.86	1.96	2.811 (2)	169

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