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Acta Cryst. (2007). E63, m2876    [ doi:10.1107/S1600536807054141 ]

catena-Poly[[aqua(4,4'-bipyridine-[kappa]N)manganese(II)]-[mu]-imidazole-4,5-dicarboxylato-[kappa]4N3,O4:O4',O5]

C. Qin and E.-B. Wang

Abstract top

In the crystal structure of the title compound, [Mn(C5H2N2O4)(C10H8N2)(H2O)]n, the Mn atom is coordinated by three O atoms, two N atoms and one water molecule in a distorted octahedral geometry. Mn atoms are connected via the imidazole-4,5-dicarboxylate anions into chains, which are further connected by intermolecular N-H...O, O-H...N and O-H...O hydrogen bonding.

Comment top

Investigations on metal carboxylate coordination polymers have become of increasing interest in the past few years Wang et al. 2005; Hao et al. 2005). As a part of our ongoing investigations in this field we report here the crystal structure of the title compound. In the crystal structure of the title compound the Mn atoms are coordinated by one oxygen atom of a water molecule, one nitrogen atom of a 4,4'-bipyridine ligand, one N and one O atom of an imidazole-4,5-dicarboxylate anion and one carboxylate group of a symmetry related imidazole-4,5-dicarboxylate anion within a distorted octahedral coordination geometry (Figure 1). The manganese atoms are linked by the anions into chains that elongate in the direction of the crystallographic b axis. These chains are further connected by N—H···O, O—H···N and O—H···O hydrogen bonding into a three-dimensional network (Tab. 1).

Related literature top

For general background, see: Wang et al. (2005). For related structures, see: Hao et al. (2005).

Experimental top

A mixture of MnCl2 (0.5 mmol), imidazole-4,5-dicarboxylic acid (0.5 mmol), 4,4'-bipyridine (0.8 mmol), and water (10 ml) was stirred for 20 min and then transferred into a 23 ml Teflon reactor. The reactor was kept at 433 K for 120 h under autogenous pressure. Single crystals of (I) were obtained after cooling to room temperature.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93 Å and N—H = 0.86 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C,N). The H atoms of the water molecule were located in difference map, their bond lengths were set to 0.85 Å and afterwards they were refined using a riding model with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997.

Figures top
[Figure 1] Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level.
catena-Poly[[aqua(4,4'-bipyridine-κN)manganese(II)]-µ-imidazole-4,5- dicarboxylato-κ4N3,O4:O4',O5] top
Crystal data top
[Mn(C5H2N2O4)(C10H8N2)(H2O1)]F000 = 780
Mr = 383.23Dx = 1.626 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14768 reflections
a = 14.051 (3) Åθ = 3.0–27.5º
b = 8.2084 (16) ŵ = 0.88 mm−1
c = 13.979 (3) ÅT = 298 (2) K
β = 103.80 (3)ºBlock, colorless
V = 1565.8 (5) Å30.24 × 0.18 × 0.17 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer		3585 independent reflections
Radiation source: fine-focus sealed tube3170 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 298(2) Kθmax = 27.5º
ω scansθmin = 3.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −18→18
Tmin = 0.817, Tmax = 0.865k = −10→10
14768 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.074  w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4434P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3585 reflectionsΔρmax = 0.30 e Å−3
228 parametersΔρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Mn(C5H2N2O4)(C10H8N2)(H2O1)]V = 1565.8 (5) Å3
Mr = 383.23Z = 4
Monoclinic, P21/cMo Kα
a = 14.051 (3) ŵ = 0.88 mm−1
b = 8.2084 (16) ÅT = 298 (2) K
c = 13.979 (3) Å0.24 × 0.18 × 0.17 mm
β = 103.80 (3)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		3585 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3170 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.865Rint = 0.025
14768 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028228 parameters
wR(F2) = 0.074H-atom parameters constrained
S = 1.08Δρmax = 0.30 e Å−3
3585 reflectionsΔρmin = −0.24 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.655818 (15)0.01342 (3)0.319366 (15)0.01988 (8)
C10.54650 (12)0.1764 (2)0.48789 (11)0.0298 (3)
H1A0.59250.15060.54560.036*
C20.47557 (10)0.21157 (17)0.33523 (10)0.0205 (3)
C30.41124 (11)0.26685 (17)0.38842 (10)0.0218 (3)
C40.47212 (10)0.20023 (17)0.22797 (10)0.0211 (3)
C50.30854 (11)0.33264 (18)0.36474 (11)0.0240 (3)
C60.84725 (13)0.2004 (2)0.31644 (14)0.0353 (4)
H6A0.86340.09350.30490.042*
C70.92054 (13)0.3157 (2)0.33212 (14)0.0349 (4)
H7A0.98440.28550.33220.042*
C80.89897 (12)0.47683 (18)0.34779 (12)0.0280 (3)
C90.80176 (14)0.5129 (2)0.34472 (18)0.0451 (5)
H9A0.78290.61970.35230.054*
C100.73332 (13)0.3891 (2)0.33030 (17)0.0432 (5)
H10A0.66890.41560.32990.052*
C111.14620 (13)0.6796 (2)0.42065 (14)0.0407 (4)
H11A1.21170.64820.43510.049*
C121.07570 (13)0.5603 (2)0.39433 (14)0.0383 (4)
H12A1.09410.45180.39220.046*
C130.97745 (12)0.60229 (19)0.37104 (12)0.0292 (3)
C140.95562 (14)0.7667 (2)0.37459 (17)0.0446 (5)
H14A0.89090.80230.35850.054*
C151.03154 (15)0.8763 (2)0.40235 (17)0.0497 (5)
H15A1.01560.98600.40430.060*
N10.55941 (9)0.15294 (16)0.39850 (9)0.0250 (3)
N20.45860 (10)0.24189 (17)0.48485 (9)0.0277 (3)
H2A0.43570.26450.53510.033*
N30.75455 (10)0.23313 (16)0.31690 (10)0.0302 (3)
N41.12591 (11)0.83635 (19)0.42656 (12)0.0411 (4)
O10.40748 (8)0.27583 (13)0.16630 (7)0.0267 (2)
O20.53640 (9)0.11390 (15)0.20466 (7)0.0329 (3)
O30.27564 (8)0.39872 (14)0.28237 (8)0.0289 (2)
O40.26300 (9)0.31810 (17)0.43017 (9)0.0432 (3)
O1W0.75594 (8)−0.06111 (14)0.45556 (8)0.0335 (3)
H10.79670.00420.49080.050*
H20.7548−0.14730.48900.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01936 (12)0.02130 (12)0.01915 (11)0.00103 (8)0.00493 (8)−0.00106 (8)
C10.0283 (8)0.0426 (9)0.0173 (6)0.0069 (7)0.0032 (6)0.0028 (6)
C20.0214 (7)0.0234 (6)0.0165 (6)0.0028 (5)0.0045 (5)0.0016 (5)
C30.0250 (7)0.0238 (7)0.0175 (6)0.0029 (6)0.0071 (5)0.0026 (5)
C40.0232 (7)0.0232 (6)0.0172 (6)0.0005 (6)0.0054 (5)−0.0007 (5)
C50.0251 (7)0.0238 (7)0.0258 (7)0.0045 (6)0.0115 (6)0.0046 (6)
C60.0365 (9)0.0250 (7)0.0482 (10)−0.0016 (7)0.0178 (8)−0.0051 (7)
C70.0284 (8)0.0289 (8)0.0512 (10)−0.0011 (7)0.0171 (7)−0.0053 (7)
C80.0280 (8)0.0244 (7)0.0313 (8)−0.0023 (6)0.0066 (6)0.0003 (6)
C90.0313 (9)0.0234 (8)0.0796 (15)0.0017 (7)0.0110 (9)−0.0024 (8)
C100.0252 (8)0.0297 (8)0.0738 (13)0.0008 (7)0.0100 (8)−0.0002 (9)
C110.0272 (8)0.0425 (10)0.0492 (10)−0.0043 (7)0.0030 (8)−0.0037 (8)
C120.0318 (9)0.0300 (8)0.0515 (10)−0.0002 (7)0.0068 (8)−0.0035 (8)
C130.0291 (8)0.0259 (7)0.0318 (8)−0.0026 (6)0.0061 (6)−0.0022 (6)
C140.0314 (9)0.0280 (8)0.0699 (13)−0.0004 (7)0.0030 (9)−0.0051 (9)
C150.0438 (11)0.0262 (8)0.0734 (14)−0.0043 (8)0.0023 (10)−0.0076 (9)
N10.0230 (6)0.0341 (7)0.0177 (5)0.0055 (5)0.0043 (5)0.0017 (5)
N20.0314 (7)0.0376 (7)0.0157 (5)0.0069 (6)0.0087 (5)0.0009 (5)
N30.0291 (7)0.0265 (6)0.0355 (7)−0.0035 (5)0.0084 (6)0.0009 (6)
N40.0371 (8)0.0382 (8)0.0434 (8)−0.0112 (7)0.0003 (7)−0.0048 (7)
O10.0304 (6)0.0332 (6)0.0159 (4)0.0109 (5)0.0044 (4)0.0028 (4)
O20.0347 (6)0.0458 (7)0.0185 (5)0.0190 (5)0.0069 (4)0.0000 (5)
O30.0235 (5)0.0364 (6)0.0282 (5)0.0051 (5)0.0090 (4)0.0116 (5)
O40.0412 (7)0.0554 (8)0.0424 (7)0.0229 (6)0.0284 (6)0.0240 (6)
O1W0.0351 (6)0.0305 (6)0.0281 (5)−0.0091 (5)−0.0060 (5)0.0048 (5)
Geometric parameters (Å, °) top
Mn1—O3i2.1190 (11)C7—H7A0.9300
Mn1—O1W2.1680 (13)C8—C91.388 (2)
Mn1—O1i2.1725 (11)C8—C131.487 (2)
Mn1—O22.1870 (13)C9—C101.380 (3)
Mn1—N12.2550 (13)C9—H9A0.9300
Mn1—N32.2805 (14)C10—N31.338 (2)
C1—N11.3190 (19)C10—H10A0.9300
C1—N21.338 (2)C11—N41.325 (3)
C1—H1A0.9300C11—C121.379 (3)
C2—C31.3772 (19)C11—H11A0.9300
C2—N11.3800 (18)C12—C131.384 (2)
C2—C41.4915 (18)C12—H12A0.9300
C3—N21.3689 (18)C13—C141.387 (2)
C3—C51.502 (2)C14—C151.379 (3)
C4—O21.2509 (18)C14—H14A0.9300
C4—O11.2567 (18)C15—N41.329 (3)
C5—O41.2409 (18)C15—H15A0.9300
C5—O31.2569 (18)N2—H2A0.8600
C6—N31.331 (2)O1—Mn1ii2.1725 (11)
C6—C71.377 (2)O3—Mn1ii2.1190 (11)
C6—H6A0.9300O1W—H10.8499
C7—C81.386 (2)O1W—H20.8500
O3i—Mn1—O1W99.23 (5)C9—C8—C13122.15 (15)
O3i—Mn1—O1i85.68 (4)C10—C9—C8119.60 (16)
O1W—Mn1—O1i81.94 (4)C10—C9—H9A120.2
O3i—Mn1—O293.87 (4)C8—C9—H9A120.2
O1W—Mn1—O2166.88 (5)N3—C10—C9123.64 (17)
O1i—Mn1—O298.44 (5)N3—C10—H10A118.2
O3i—Mn1—N1167.76 (4)C9—C10—H10A118.2
O1W—Mn1—N193.00 (5)N4—C11—C12123.70 (17)
O1i—Mn1—N195.95 (5)N4—C11—H11A118.2
O2—Mn1—N173.89 (4)C12—C11—H11A118.2
O3i—Mn1—N388.03 (5)C11—C12—C13119.90 (17)
O1W—Mn1—N388.10 (5)C11—C12—H12A120.0
O1i—Mn1—N3167.21 (5)C13—C12—H12A120.0
O2—Mn1—N393.08 (5)C12—C13—C14116.77 (16)
N1—Mn1—N392.56 (5)C12—C13—C8121.66 (15)
N1—C1—N2111.28 (13)C14—C13—C8121.52 (15)
N1—C1—H1A124.4C15—C14—C13118.82 (17)
N2—C1—H1A124.4C15—C14—H14A120.6
C3—C2—N1109.80 (12)C13—C14—H14A120.6
C3—C2—C4134.05 (13)N4—C15—C14124.66 (18)
N1—C2—C4116.14 (12)N4—C15—H15A117.7
N2—C3—C2104.77 (12)C14—C15—H15A117.7
N2—C3—C5119.12 (13)C1—N1—C2105.49 (12)
C2—C3—C5136.00 (13)C1—N1—Mn1140.65 (11)
O2—C4—O1123.34 (13)C2—N1—Mn1112.55 (9)
O2—C4—C2116.41 (12)C1—N2—C3108.64 (12)
O1—C4—C2120.24 (13)C1—N2—H2A125.7
O4—C5—O3125.12 (14)C3—N2—H2A125.7
O4—C5—C3116.12 (13)C6—N3—C10116.42 (14)
O3—C5—C3118.76 (13)C6—N3—Mn1116.08 (11)
N3—C6—C7123.76 (15)C10—N3—Mn1126.72 (12)
N3—C6—H6A118.1C11—N4—C15116.11 (16)
C7—C6—H6A118.1C4—O1—Mn1ii128.66 (9)
C6—C7—C8119.84 (16)C4—O2—Mn1119.87 (9)
C6—C7—H7A120.1C5—O3—Mn1ii132.84 (10)
C8—C7—H7A120.1Mn1—O1W—H1122.5
C7—C8—C9116.69 (15)Mn1—O1W—H2128.7
C7—C8—C13121.11 (15)H1—O1W—H2107.7
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1iii0.861.992.8002 (17)156
N2—H2A···O2iii0.862.653.2305 (18)126
O1W—H1···N4iv0.851.912.7513 (19)173
O1W—H2···O4v0.851.852.6972 (17)171
Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.861.992.8002 (17)156
N2—H2A···O2i0.862.653.2305 (18)126
O1W—H1···N4ii0.851.912.7513 (19)173
O1W—H2···O4iii0.851.852.6972 (17)171
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y, −z+1.
Acknowledgements top

This work was financially supported by the National Natural Science Foundation of China (No. 20701006), the Foundation for Excellent Youth of Jilin, China (Grant No. 20070103), and the Science Foundation for Young Teachers of Northeast Normal University (No. 20070303).

references
References top

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