Diaqua-[5,5'-dicarb-oxy-2,2'-(propane-1,3-di-yl)bis-(1H-imidazole-4-carboxyl-ato)]manganese(II).

The complex mol-ecule of the title compound, [Mn(C(13)H(10)N(4)O(8))(H(2)O)(2)] or [Mn(H(4)pbidc)(H(2)O)(2)] (H(6)pbidc = 2,2'-(propane-1,3-di-yl)bis-(1H-imidazole-4,5-dicarb-oxy-lic acid), has 2 symmetry with the twofold rotation axis running through the Mn(2+) cation and the central C atom of the propanediyl unit. The cation is six-coordinated by two N atoms and two O atoms from one H(4)pbidc(2-) anion and two water O atoms in a considerably distorted octa-hedral coordination. In the crystal, adjacent mol-ecules are linked through O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background to complexes based on 1H-imidazole-4,5-dicarb­oxy­lic acid, see: Ghosh et al. (2009 ▶); Liu et al. (2008 ▶); Sun & Yang (2007 ▶).

Experimental

Crystal data

[Mn(C13H10N4O8)(H2O)2]

M = 441.22

Monoclinic,

a = 15.620 (3) Å

b = 8.5310 (17) Å

c = 12.739 (3) Å

β = 97.07 (3)°

V = 1684.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.85 mm−1

T = 293 K

0.23 × 0.21 × 0.18 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.828, T max = 0.862

3426 measured reflections

1464 independent reflections

1265 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.09

1464 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012566/wm2475sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012566/wm2475Isup2.hkl

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

[Mn(C13H10N4O8)(H2O)2]	F(000) = 900
Mr = 441.22	Dx = 1.740 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2738 reflections
a = 15.620 (3) Å	θ = 2.6–27.9°
b = 8.5310 (17) Å	µ = 0.85 mm−1
c = 12.739 (3) Å	T = 293 K
β = 97.07 (3)°	Prism, light yellow
V = 1684.7 (6) Å3	0.23 × 0.21 × 0.18 mm
Z = 4

Rigaku Saturn diffractometer	1464 independent reflections
Radiation source: fine-focus sealed tube	1265 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −17→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −10→8
Tmin = 0.828, Tmax = 0.862	l = −15→12
3426 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0405P)2 + 1.7694P] where P = (Fo2 + 2Fc2)/3
1464 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.45 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	0.0000	0.22580 (7)	0.2500	0.0249 (2)
N1	0.08997 (14)	0.4109 (3)	0.32272 (18)	0.0273 (5)
N2	0.16454 (14)	0.5985 (3)	0.40995 (19)	0.0308 (6)
H2A	0.1767	0.6876	0.4397	0.037*
O1	0.13833 (12)	0.1209 (2)	0.26815 (16)	0.0336 (5)
O2	0.27378 (12)	0.1518 (2)	0.34234 (17)	0.0382 (5)
O3	0.35729 (12)	0.3642 (2)	0.44866 (16)	0.0336 (5)
H3	0.3281	0.2937	0.4133	0.040*
O4	0.34141 (12)	0.6152 (2)	0.48617 (17)	0.0370 (5)
O5	0.00284 (13)	0.1299 (3)	0.09807 (16)	0.0466 (6)
H1W	−0.0390	0.1314	0.0487	0.056*
H2W	0.0460	0.1216	0.0637	0.056*
C1	0.19523 (18)	0.2024 (3)	0.3170 (2)	0.0278 (6)
C2	0.17401 (16)	0.3615 (3)	0.3491 (2)	0.0242 (6)
C3	0.22101 (16)	0.4777 (3)	0.4038 (2)	0.0258 (6)
C4	0.31248 (17)	0.4881 (3)	0.4495 (2)	0.0269 (6)
C5	0.08645 (17)	0.5546 (3)	0.3616 (2)	0.0297 (7)
C6	0.00932 (19)	0.6586 (4)	0.3507 (3)	0.0462 (9)
H6A	0.0130	0.7285	0.4111	0.055*
H6B	−0.0420	0.5947	0.3516	0.055*
C7	0.0000	0.7559 (5)	0.2500	0.0562 (15)
H7A	−0.0509	0.8214	0.2480	0.067*

	U11	U22	U33	U12	U13	U23
Mn1	0.0183 (3)	0.0268 (3)	0.0276 (3)	0.000	−0.0048 (2)	0.000
N1	0.0177 (11)	0.0278 (12)	0.0344 (13)	0.0007 (9)	−0.0048 (10)	−0.0048 (10)
N2	0.0222 (12)	0.0279 (12)	0.0396 (14)	−0.0003 (10)	−0.0068 (11)	−0.0085 (10)
O1	0.0237 (11)	0.0333 (11)	0.0416 (12)	0.0003 (9)	−0.0051 (9)	−0.0114 (9)
O2	0.0227 (11)	0.0373 (12)	0.0515 (13)	0.0084 (9)	−0.0078 (10)	−0.0074 (10)
O3	0.0208 (10)	0.0361 (12)	0.0408 (11)	−0.0011 (9)	−0.0094 (9)	−0.0059 (9)
O4	0.0236 (10)	0.0357 (12)	0.0490 (13)	−0.0055 (9)	−0.0062 (10)	−0.0099 (10)
O5	0.0241 (11)	0.0804 (17)	0.0328 (12)	0.0111 (11)	−0.0070 (10)	−0.0179 (11)
C1	0.0238 (15)	0.0319 (15)	0.0268 (14)	0.0015 (12)	−0.0008 (12)	−0.0008 (12)
C2	0.0174 (13)	0.0281 (14)	0.0262 (14)	0.0001 (11)	−0.0008 (12)	0.0002 (11)
C3	0.0191 (14)	0.0291 (14)	0.0278 (14)	−0.0010 (11)	−0.0028 (11)	−0.0012 (12)
C4	0.0206 (14)	0.0331 (16)	0.0261 (14)	−0.0018 (12)	−0.0002 (12)	0.0023 (12)
C5	0.0189 (14)	0.0298 (15)	0.0381 (16)	0.0004 (12)	−0.0054 (13)	−0.0094 (13)
C6	0.0235 (16)	0.0419 (18)	0.069 (2)	0.0065 (14)	−0.0091 (16)	−0.0271 (17)
C7	0.029 (2)	0.023 (2)	0.109 (5)	0.000	−0.020 (3)	0.000

Mn1—O5	2.107 (2)	O3—H3	0.8500
Mn1—O5i	2.107 (2)	O4—C4	1.243 (3)
Mn1—N1	2.237 (2)	O5—H1W	0.8501
Mn1—N1i	2.237 (2)	O5—H2W	0.8500
Mn1—O1	2.3236 (19)	C1—C2	1.467 (4)
Mn1—O1i	2.3236 (19)	C2—C3	1.371 (4)
N1—C5	1.326 (3)	C3—C4	1.478 (4)
N1—C2	1.380 (3)	C5—C6	1.489 (4)
N2—C5	1.350 (3)	C6—C7	1.520 (4)
N2—C3	1.365 (3)	C6—H6A	0.9700
N2—H2A	0.8600	C6—H6B	0.9700
O1—C1	1.235 (3)	C7—C6i	1.520 (4)
O2—C1	1.303 (3)	C7—H7A	0.9700
O3—C4	1.269 (3)
O5—Mn1—O5i	134.29 (13)	H1W—O5—H2W	101.9
O5—Mn1—N1	124.84 (9)	O1—C1—O2	122.4 (3)
O5i—Mn1—N1	88.68 (8)	O1—C1—C2	119.2 (2)
O5—Mn1—N1i	88.68 (8)	O2—C1—C2	118.4 (2)
O5i—Mn1—N1i	124.84 (9)	C3—C2—N1	109.7 (2)
N1—Mn1—N1i	90.22 (11)	C3—C2—C1	133.2 (2)
O5—Mn1—O1	79.48 (8)	N1—C2—C1	117.1 (2)
O5i—Mn1—O1	83.31 (8)	N2—C3—C2	105.4 (2)
N1—Mn1—O1	72.64 (7)	N2—C3—C4	122.2 (2)
N1i—Mn1—O1	147.34 (8)	C2—C3—C4	132.4 (2)
O5—Mn1—O1i	83.31 (8)	O4—C4—O3	123.7 (2)
O5i—Mn1—O1i	79.48 (8)	O4—C4—C3	119.3 (2)
N1—Mn1—O1i	147.34 (8)	O3—C4—C3	117.0 (2)
N1i—Mn1—O1i	72.64 (7)	N1—C5—N2	110.5 (2)
O1—Mn1—O1i	134.71 (10)	N1—C5—C6	125.9 (2)
C5—N1—C2	105.8 (2)	N2—C5—C6	123.5 (2)
C5—N1—Mn1	138.97 (18)	C5—C6—C7	113.4 (3)
C2—N1—Mn1	114.56 (17)	C5—C6—H6A	108.9
C5—N2—C3	108.6 (2)	C7—C6—H6A	108.9
C5—N2—H2A	125.7	C5—C6—H6B	108.9
C3—N2—H2A	125.7	C7—C6—H6B	108.9
C1—O1—Mn1	115.86 (17)	H6A—C6—H6B	107.7
C4—O3—H3	109.4	C6i—C7—C6	113.7 (3)
Mn1—O5—H1W	124.9	C6i—C7—H7A	107.4
Mn1—O5—H2W	127.8	C6—C7—H7A	109.3
O5—Mn1—N1—C5	121.0 (3)	O2—C1—C2—C3	−0.1 (5)
O5i—Mn1—N1—C5	−92.4 (3)	O1—C1—C2—N1	0.3 (4)
N1i—Mn1—N1—C5	32.5 (3)	O2—C1—C2—N1	−178.9 (2)
O1—Mn1—N1—C5	−175.8 (3)	C5—N2—C3—C2	0.6 (3)
O1i—Mn1—N1—C5	−24.3 (4)	C5—N2—C3—C4	−179.9 (2)
O5—Mn1—N1—C2	−69.7 (2)	N1—C2—C3—N2	−0.2 (3)
O5i—Mn1—N1—C2	76.92 (19)	C1—C2—C3—N2	−179.0 (3)
N1i—Mn1—N1—C2	−158.2 (2)	N1—C2—C3—C4	−179.5 (3)
O1—Mn1—N1—C2	−6.49 (17)	C1—C2—C3—C4	1.6 (5)
O1i—Mn1—N1—C2	144.92 (17)	N2—C3—C4—O4	−6.9 (4)
O5—Mn1—O1—C1	138.8 (2)	C2—C3—C4—O4	172.4 (3)
O5i—Mn1—O1—C1	−83.7 (2)	N2—C3—C4—O3	173.2 (3)
N1—Mn1—O1—C1	7.01 (19)	C2—C3—C4—O3	−7.5 (4)
N1i—Mn1—O1—C1	68.3 (3)	C2—N1—C5—N2	0.8 (3)
O1i—Mn1—O1—C1	−151.7 (2)	Mn1—N1—C5—N2	170.6 (2)
Mn1—O1—C1—O2	172.9 (2)	C2—N1—C5—C6	178.2 (3)
Mn1—O1—C1—C2	−6.3 (3)	Mn1—N1—C5—C6	−11.9 (5)
C5—N1—C2—C3	−0.4 (3)	C3—N2—C5—N1	−0.9 (3)
Mn1—N1—C2—C3	−173.07 (18)	C3—N2—C5—C6	−178.5 (3)
C5—N1—C2—C1	178.7 (2)	N1—C5—C6—C7	−87.0 (4)
Mn1—N1—C2—C1	6.0 (3)	N2—C5—C6—C7	90.1 (4)
O1—C1—C2—C3	179.1 (3)	C5—C6—C7—C6i	60.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2W···O4ii	0.85	1.94	2.780 (3)	168
O5—H1W···O3iii	0.85	1.93	2.780 (3)	174
N2—H2A···O4iv	0.86	1.97	2.785 (3)	159
O3—H3···O2	0.85	1.68	2.527 (3)	178

Table 1

Selected bond lengths (Å)

Mn1—O5	2.107 (2)
Mn1—N1	2.237 (2)
Mn1—O1	2.3236 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H2W⋯O4i	0.85	1.94	2.780 (3)	168
O5—H1W⋯O3ii	0.85	1.93	2.780 (3)	174
N2—H2A⋯O4iii	0.86	1.97	2.785 (3)	159
O3—H3⋯O2	0.85	1.68	2.527 (3)	178

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