PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m151.
Published online 2010 January 13. doi:  10.1107/S1600536810001029
PMCID: PMC2979947

Poly[diaqua­(μ3-1H-benzimidazole-5,6-dicarboxyl­ato-κ4 N 3:O 5,O 6:O 6′)magnesium(II)]

Abstract

In the title complex, [Mg(C9H4N2O4)(H2O)2]n, the MgII atom is six-coordinated by one N and three O atoms from three different 1H-benzimidazole-5,6-dicarboxyl­ate ligands and two O atoms from two water mol­ecules, forming a slightly distorted octa­hedral geometry. The ligand links the MgII centres into a three-dimensional network. Extensive N—H(...)O and O—H(...)O hydrogen bonds exist between the ligands and water mol­ecules, stabilizing the crystal structure.

Related literature

For related structures of 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Song, Wang, Hu et al. (2009 [triangle]); Song, Wang, Li et al. (2009 [triangle]); Song, Wang, Qin et al. (2009 [triangle]); Wang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m151-scheme1.jpg

Experimental

Crystal data

  • [Mg(C9H4N2O4)(H2O)2]
  • M r = 264.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m151-efi4.jpg
  • a = 7.4793 (15) Å
  • b = 18.958 (4) Å
  • c = 7.3132 (15) Å
  • β = 99.38 (3)°
  • V = 1023.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.21 mm

Data collection

  • Rigaku/MSC Mercury CCD diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.943, T max = 0.960
  • 4611 measured reflections
  • 1143 independent reflections
  • 1096 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.090
  • S = 1.06
  • 1143 reflections
  • 163 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: CrystalStructure (Rigaku/MSC, 2002 [triangle]); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001029/hy2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001029/hy2269Isup2.hkl

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

Acknowledgments

The authors acknowledge Guang Dong Ocean University for supporting this work.

supplementary crystallographic information

Comment

1H-Benzimidazole-5,6-dicarboxylic acid (H2L) can function as a multidentate ligand and several complexes formed from this ligand have been reported recently, including catena-poly[[diaqua(1,10-phenanthroline-κ2N,N') nickel(II)]-µ-L2N3:O6] (Song, Wang, Hu et al., 2009), pentaaqua(LN3)cobalt(II) pentahydrate (Song, Wang, Li et al., 2009), pentaaqua(LN3)nickel(II) pentahydrate (Song, Wang, Qin et al., 2009) and tetraaquabis(LN3)cobalt(II) dimethylformamide disolvate dihydrate (Wang et al., 2009). However, the Mg complex of the H2L ligand has not been reported up to now.

As shown in Fig. 1, the MgII atom is six-coordinated by one N and three O atoms from three different L ligands, and two O atoms from two water molecules (Table 1), showing a slightly distorted octahedral geometry. The equatorial plane is defined by O1W, O2W, O1i and O3i atoms, while N1 and O4ii occupy the axial positions [symmetry codes: (i) x, 1 - y, -1/2 + z; (ii) 1/2 + x, 1/2 + y, z]. Intermolecular O—H···O and N—H···O hydrogen bonds between the ligand and the coordinated water molecules stabilize the structure (Table 2 and Fig 2).

Experimental

A mixture of MgCl2 (1.0 mmol), H2L (0.6 mmol), CH3CN (6 ml) and water (4 ml) was added to a 20 ml Teflon-lined stainless container, which was heated to 150°C and held at that temperature for 5 d. After cooling to room temperature, colourless crystals were recovered by filtration.

Refinement

C– and N-bound H atoms were placed at calculated positions and treated as riding on the parent C or N atoms, with C—H = 0.93 and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C, N). The water H atoms were located in a difference Fourier map and refined as riding with a distance restraint of O—H = 0.84 Å and with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The structure of the title compound, showing the 30% probability displacement ellipsoids. [Symmetry codes: (i) x, 1 - y, -1/2 + z; (ii) 1/2 + x, 1/2 + y, z.]
Fig. 2.
A view of the three-dimensional network structure of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

[Mg(C9H4N2O4)(H2O)2]F(000) = 544
Mr = 264.48Dx = 1.717 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 4114 reflections
a = 7.4793 (15) Åθ = 3.6–27.5°
b = 18.958 (4) ŵ = 0.20 mm1
c = 7.3132 (15) ÅT = 293 K
β = 99.38 (3)°Block, colourless
V = 1023.1 (4) Å30.30 × 0.25 × 0.21 mm
Z = 4

Data collection

Rigaku/MSC Mercury CCD diffractometer1143 independent reflections
Radiation source: fine-focus sealed tube1096 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)h = −9→9
Tmin = 0.943, Tmax = 0.960k = −24→24
4611 measured reflectionsl = −8→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.04P)2 + 2P] where P = (Fo2 + 2Fc2)/3
1143 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.38 e Å3
2 restraintsΔρmin = −0.25 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Mg10.27807 (16)0.68928 (5)0.63241 (16)0.0172 (3)
O10.4349 (4)0.37147 (14)0.9888 (4)0.0234 (5)
O20.5047 (4)0.37926 (16)0.7087 (4)0.0317 (7)
O30.1320 (4)0.28489 (12)0.8699 (4)0.0237 (6)
O4−0.0733 (4)0.28304 (12)0.6132 (3)0.0236 (6)
N10.0678 (5)0.61142 (15)0.6633 (5)0.0214 (6)
N3−0.2035 (5)0.56134 (16)0.6122 (5)0.0271 (7)
H3−0.31960.55770.58740.033*
C10.0380 (5)0.31481 (16)0.7326 (5)0.0173 (6)
C20.0549 (5)0.39389 (16)0.7123 (5)0.0182 (7)
C3−0.1002 (5)0.43318 (18)0.6560 (5)0.0223 (7)
H2−0.21270.41160.62400.027*
C4−0.0816 (5)0.50629 (18)0.6490 (5)0.0206 (7)
C50.0876 (5)0.53907 (17)0.6828 (5)0.0184 (7)
C60.2438 (5)0.49930 (18)0.7332 (5)0.0185 (7)
H10.35740.52060.75310.022*
C70.2259 (4)0.42738 (16)0.7529 (4)0.0154 (6)
C80.3985 (5)0.38839 (17)0.8204 (5)0.0173 (7)
C9−0.1073 (6)0.62155 (18)0.6224 (6)0.0262 (8)
H9−0.15990.66590.60230.031*
O1W0.4663 (4)0.65596 (14)0.8537 (4)0.0289 (6)
H1W0.45730.64080.95980.043*
H2W0.53550.69110.86010.043*
O2W0.1388 (5)0.75021 (15)0.7982 (5)0.0374 (8)
H3W0.06600.73420.86390.056*
H4W0.11760.79270.77040.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mg10.0191 (6)0.0134 (4)0.0184 (5)−0.0004 (4)0.0009 (4)0.0004 (4)
O10.0186 (13)0.0310 (13)0.0202 (12)0.0004 (10)0.0019 (11)0.0074 (10)
O20.0247 (16)0.0462 (17)0.0253 (14)0.0133 (12)0.0075 (12)0.0005 (12)
O30.0274 (14)0.0165 (11)0.0235 (12)−0.0008 (10)−0.0074 (11)0.0006 (9)
O40.0281 (15)0.0195 (12)0.0203 (13)−0.0067 (10)−0.0045 (11)0.0014 (9)
N10.0215 (16)0.0167 (13)0.0265 (15)0.0018 (11)0.0058 (12)0.0039 (11)
N30.0147 (16)0.0249 (14)0.0400 (19)0.0032 (12)−0.0009 (14)0.0065 (13)
C10.0195 (17)0.0151 (13)0.0175 (16)−0.0016 (12)0.0043 (14)−0.0002 (11)
C20.0197 (18)0.0150 (14)0.0192 (16)−0.0024 (12)0.0008 (14)0.0015 (12)
C30.0184 (18)0.0204 (16)0.0274 (19)−0.0040 (13)0.0011 (15)0.0023 (13)
C40.0151 (19)0.0216 (16)0.0244 (18)0.0023 (12)0.0011 (14)0.0045 (13)
C50.0191 (17)0.0160 (14)0.0203 (16)−0.0019 (12)0.0035 (14)0.0016 (12)
C60.0129 (16)0.0198 (15)0.0224 (17)−0.0022 (11)0.0018 (14)0.0008 (12)
C70.0151 (16)0.0178 (14)0.0134 (14)0.0002 (12)0.0027 (13)−0.0002 (11)
C80.0154 (17)0.0154 (14)0.0204 (17)−0.0024 (11)0.0007 (14)−0.0011 (11)
C90.024 (2)0.0208 (16)0.034 (2)0.0068 (14)0.0050 (17)0.0067 (14)
O1W0.0340 (15)0.0271 (13)0.0225 (12)−0.0071 (11)−0.0043 (12)0.0052 (10)
O2W0.0486 (19)0.0219 (12)0.0476 (19)0.0063 (12)0.0251 (16)−0.0022 (12)

Geometric parameters (Å, °)

Mg1—N12.195 (3)C1—C21.514 (4)
Mg1—O1i2.051 (3)C2—C31.384 (5)
Mg1—O3i2.106 (3)C2—C71.416 (5)
Mg1—O4ii2.113 (3)C3—C41.395 (5)
Mg1—O1W2.063 (3)C3—H20.9300
Mg1—O2W2.074 (3)C4—C51.395 (5)
O1—C81.259 (4)C5—C61.388 (5)
O2—C81.241 (4)C6—C71.380 (5)
O3—C11.263 (4)C6—H10.9300
O4—C11.257 (4)C7—C81.499 (5)
N1—C91.310 (5)C9—H90.9300
N1—C51.384 (4)O1W—H1W0.8401
N3—C91.345 (5)O1W—H2W0.8400
N3—C41.383 (5)O2W—H3W0.8399
N3—H30.8600O2W—H4W0.8400
O1i—Mg1—O1W81.69 (12)C7—C2—C1120.7 (3)
O1i—Mg1—O2W174.71 (15)C2—C3—C4117.5 (3)
O1W—Mg1—O2W93.18 (14)C2—C3—H2121.2
O1i—Mg1—O3i85.34 (12)C4—C3—H2121.3
O1W—Mg1—O3i166.51 (13)N3—C4—C3133.6 (3)
O2W—Mg1—O3i99.68 (13)N3—C4—C5104.4 (3)
O1i—Mg1—O4ii95.02 (12)C3—C4—C5122.0 (3)
O1W—Mg1—O4ii90.61 (11)N1—C5—C6129.5 (3)
O2W—Mg1—O4ii83.68 (12)N1—C5—C4110.1 (3)
O3i—Mg1—O4ii86.80 (11)C6—C5—C4120.3 (3)
O1i—Mg1—N198.87 (12)C7—C6—C5118.2 (3)
O1W—Mg1—N197.00 (12)C7—C6—H1120.9
O2W—Mg1—N182.98 (13)C5—C6—H1120.9
O3i—Mg1—N188.65 (12)C6—C7—C2121.4 (3)
O4ii—Mg1—N1164.98 (12)C6—C7—C8115.4 (3)
C8—O1—Mg1iii126.4 (2)C2—C7—C8123.2 (3)
C1—O3—Mg1iii139.4 (2)O2—C8—O1123.3 (3)
C1—O4—Mg1iv130.8 (2)O2—C8—C7117.5 (3)
C9—N1—C5104.8 (3)O1—C8—C7119.0 (3)
C9—N1—Mg1125.8 (2)N1—C9—N3113.2 (3)
C5—N1—Mg1127.6 (3)N1—C9—H9123.4
C9—N3—C4107.4 (3)N3—C9—H9123.4
C9—N3—H3126.3Mg1—O1W—H1W133.0
C4—N3—H3126.3Mg1—O1W—H2W97.9
O4—C1—O3123.8 (3)H1W—O1W—H2W111.1
O4—C1—C2117.6 (3)Mg1—O2W—H3W124.6
O3—C1—C2118.6 (3)Mg1—O2W—H4W119.1
C3—C2—C7120.4 (3)H3W—O2W—H4W111.8
C3—C2—C1118.9 (3)

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, y+1/2, z; (iii) x, −y+1, z+1/2; (iv) x−1/2, y−1/2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O1v0.862.292.992 (4)138
O1W—H1W···O2iii0.841.842.651 (4)163
O1W—H2W···O3ii0.841.922.734 (4)164
O2W—H3W···O4iii0.842.273.068 (4)160
O2W—H4W···O2vi0.841.872.685 (4)164

Symmetry codes: (v) x−1, −y+1, z−1/2; (iii) x, −y+1, z+1/2; (ii) x+1/2, y+1/2, z; (vi) x−1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2269).

References

  • Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
  • Jacobson, R. (1998). REQAB. Private communication to Molecular Structure Corporation, The Woodlands, Texas, USA.
  • Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, W.-D., Wang, H., Hu, S.-W., Qin, P.-W. & Li, S.-J. (2009). Acta Cryst. E65, m701. [PMC free article] [PubMed]
  • Song, W.-D., Wang, H., Li, S.-J., Qin, P.-W. & Hu, S.-W. (2009). Acta Cryst. E65, m702. [PMC free article] [PubMed]
  • Song, W.-D., Wang, H., Qin, P.-W., Li, S.-J. & Hu, S.-W. (2009). Acta Cryst. E65, m672. [PMC free article] [PubMed]
  • Wang, H., Song, W.-D., Li, S.-J., Miao, D.-L. & Liu, J. (2009). Acta Cryst. E65, m1423. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography