metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­aqua­bis­(5-carb­­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2N3,O4)magnesium(II) 3.5-hydrate

aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan 467044, People's Republic of China
*Correspondence e-mail: tianlin1288@163.com

(Received 30 January 2010; accepted 11 February 2010; online 17 February 2010)

In the title complex, [Mg(C8H9N2O4)2(H2O)2]·3.5H2O, the MgII atom is six-coordinated by two N,O-bidentate 5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules, forming a distorted octa­hedral environment. The complex mol­ecules are linked into a three-dimensional network by N—H⋯O and O—H⋯O hydrogen-bonding inter­actions. The propyl groups are disordered over two sites, with site occupancies of 0.755 (7):0.245 (7) and 0.556 (13):0.444 (13).

Related literature

For related structures, see: Sengupta et al. (2001[Sengupta, P., Dinda, R., Ghosh, S. & Sheldrick, W. S. (2001). Polyhedron, 20, 3349-3354.]); Song et al. (2010[Song, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53.]); Wang et al. (2004[Wang, C.-F., Gao, E.-Q., Zheng, H. & Yan, C.-H. (2004). Chem. Commun. pp. 720-721.]); Yan et al. (2010[Yan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99.]).

[Scheme 1]

Experimental

Crystal data
  • [Mg(C8H9N2O4)2(H2O)2]·3.5H2O

  • Mr = 517.74

  • Triclinic, [P \overline 1]

  • a = 10.516 (1) Å

  • b = 10.5332 (11) Å

  • c = 11.3989 (13) Å

  • α = 83.288 (1)°

  • β = 81.783 (1)°

  • γ = 86.458 (2)°

  • V = 1239.8 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 298 K

  • 0.48 × 0.38 × 0.35 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.935, Tmax = 0.952

  • 6478 measured reflections

  • 4321 independent reflections

  • 2780 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.178

  • S = 1.00

  • 4321 reflections

  • 378 parameters

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O12 0.86 1.89 2.745 (4) 170
N4—H4⋯O13 0.86 1.91 2.737 (4) 162
O3—H3⋯O2 0.82 1.70 2.511 (3) 173
O7—H7⋯O6 0.82 1.65 2.461 (3) 172
O9—H9C⋯O8i 0.85 1.88 2.732 (3) 177
O9—H9D⋯O11ii 0.85 1.83 2.678 (4) 176
O10—H10C⋯O4iii 0.85 1.94 2.787 (3) 174
O10—H10D⋯O8iv 0.85 2.06 2.905 (3) 174
O11—H11C⋯O2v 0.85 1.95 2.794 (3) 172
O11—H11D⋯O5vi 0.85 2.05 2.893 (3) 172
O12—H12C⋯O7vi 0.85 2.05 2.888 (4) 167
O12—H12D⋯O14v 0.85 1.84 2.672 (6) 167
O13—H13C⋯O14 0.85 1.85 2.643 (6) 156
O13—H13D⋯O11vii 0.85 2.07 2.869 (5) 156
O14—H14G⋯O1viii 0.85 2.00 2.816 (5) 162
O14—H14H⋯O1ix 0.85 1.98 2.799 (5) 162
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x, y-1, z+1; (iii) -x+1, -y, -z+1; (iv) x, y-1, z; (v) -x+1, -y+1, -z+1; (vi) -x, -y+1, -z+1; (vii) x, y, z+1; (viii) x, y+1, z; (ix) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Imidazole-4,5-dicarboxylate ligands with efficient N,O-donors have been been widely used to obtain new complexes with excellent properties (Sengupta et al., 2001; Song et al.,2010; Wang et al., 2004; Yan et al., 2010). Bearing this in mind, we introduced Mg(CH3CO2)2 and 2-propyl-1H-imidazole-4,5-dicarboxylic acid into reaction so as to obtain a new MgII complex.

As illustrated in Fig. 1, the title complex molecule contains one MgII ion, two mono-deprotonated 2-propyl-1H-imidazole-4,5-dicarboxylate ligands, two coordinated water molecules and three and half uncoordinated water molecules. The Mg II atom is six-coordinated by two N,O-bidentate ligands and two water molecules in a slightly distorted octahedral environment. Both ligands coordinate through N atoms and carboxylate O atoms in a bidentate chelate fashion, forming two five-membered Mg, O, C, C, N rings. Uncoordinated solvent water molecules are located in cavities of the three-dimensional network, participating in N—H···O and O—H···O hydrogen bonds, which contribute to the stability of the network. The two propyl residues are disordered over two sites, with site occupancies of 0.755 (7):0.245 (7) and 0.556 (13):0.444 (13).

Related literature top

For related structures, see: Sengupta et al. (2001); Song et al. (2010); Wang et al. (2004); Yan et al. (2010).

Experimental top

The title compound was prepared by the hydrothermal reaction of Mg(CH3CO2)2 (0.5 mmol, 0.07 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of H2O solution. The reaction was performed in a Teflon-lined autoclave (20 ml), which was heated at 433 K for 2 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Refinement top

C- and N-bound H atoms were placed at calculated positions and were treated as riding atoms, with C—H = 0.97 (CH2) and 0.96 (CH3) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N). The water H atoms were located in a difference map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O). H atoms of carboxyl groups were located in a difference map and refined as riding, with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. A view of the three-dimensional network constructed by N—H···O and O—H···O hydrogen bonding interactions (dashed lines).
Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ2N3,O4)magnesium(II) 3.5-hydrate top
Crystal data top
[Mg(C8H9N2O4)2(H2O)2]·3.5H2OZ = 2
Mr = 517.74F(000) = 546
Triclinic, P1Dx = 1.387 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.516 (1) ÅCell parameters from 2051 reflections
b = 10.5332 (11) Åθ = 2.5–23.9°
c = 11.3989 (13) ŵ = 0.14 mm1
α = 83.288 (1)°T = 298 K
β = 81.783 (1)°Block, colorless
γ = 86.458 (2)°0.48 × 0.38 × 0.35 mm
V = 1239.8 (2) Å3
Data collection top
Bruker SMART 1000 CCD
diffractometer
4321 independent reflections
Radiation source: fine-focus sealed tube2780 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.935, Tmax = 0.952k = 712
6478 measured reflectionsl = 1213
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0865P)2 + 0.6255P]
where P = (Fo2 + 2Fc2)/3
4321 reflections(Δ/σ)max = 0.001
378 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Mg(C8H9N2O4)2(H2O)2]·3.5H2Oγ = 86.458 (2)°
Mr = 517.74V = 1239.8 (2) Å3
Triclinic, P1Z = 2
a = 10.516 (1) ÅMo Kα radiation
b = 10.5332 (11) ŵ = 0.14 mm1
c = 11.3989 (13) ÅT = 298 K
α = 83.288 (1)°0.48 × 0.38 × 0.35 mm
β = 81.783 (1)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
4321 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2780 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.952Rint = 0.028
6478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.00Δρmax = 0.58 e Å3
4321 reflectionsΔρmin = 0.31 e Å3
378 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Mg10.20602 (10)0.14342 (10)0.81297 (9)0.0417 (3)
N10.2821 (2)0.1678 (3)0.6227 (2)0.0429 (6)
N20.3556 (3)0.1891 (3)0.4316 (2)0.0518 (7)
H20.35650.20230.35560.062*
N30.2165 (2)0.3506 (2)0.8307 (2)0.0406 (6)
N40.2228 (2)0.5498 (3)0.8701 (2)0.0455 (7)
H40.25250.61920.88590.055*
O10.4034 (2)0.1060 (2)0.81403 (18)0.0481 (6)
O20.5972 (2)0.1009 (3)0.7049 (2)0.0601 (7)
O30.6855 (2)0.1268 (3)0.4872 (2)0.0639 (7)
H30.65630.11200.55780.096*
O40.6100 (2)0.1666 (2)0.3161 (2)0.0652 (7)
O50.0167 (2)0.2175 (2)0.7964 (2)0.0483 (6)
O60.1219 (2)0.3840 (2)0.8141 (2)0.0602 (7)
O70.1173 (2)0.6067 (2)0.8584 (2)0.0588 (7)
H70.11780.53040.85040.088*
O80.0222 (2)0.7397 (2)0.8968 (2)0.0580 (7)
O90.1655 (3)0.1075 (2)0.9919 (2)0.0653 (8)
H9C0.10710.15291.02900.078*
H9D0.18320.04181.03850.078*
O100.1704 (3)0.0415 (2)0.7915 (2)0.0674 (8)
H10C0.23940.07440.75690.081*
H10D0.12280.10180.82410.081*
O110.2291 (3)0.8974 (3)0.1314 (3)0.0858 (10)
H11C0.27620.89400.18640.103*
H11D0.15920.86190.15970.103*
O120.3299 (3)0.2189 (4)0.1936 (3)0.1094 (13)
H12C0.27050.26760.16710.131*
H12D0.37290.18390.13590.131*
O130.3434 (3)0.7359 (3)0.9551 (3)0.1053 (12)
H13C0.41030.77950.94190.126*
H13D0.29140.76841.00880.126*
O140.5130 (5)0.9089 (5)0.9622 (4)0.0584 (13)0.50
H14G0.48160.97840.92980.070*0.50
H14H0.53330.92201.02920.070*0.50
C10.4763 (3)0.1168 (3)0.7168 (3)0.0438 (8)
C20.4130 (3)0.1509 (3)0.6087 (3)0.0382 (7)
C30.4614 (3)0.1646 (3)0.4896 (3)0.0430 (8)
C40.5913 (3)0.1533 (3)0.4242 (3)0.0482 (8)
C50.2496 (3)0.1891 (4)0.5137 (3)0.0563 (10)
C60.1138 (11)0.1962 (10)0.4864 (9)0.064 (2)0.755 (7)
H6A0.05980.14920.55110.077*0.755 (7)
H6B0.11080.15660.41420.077*0.755 (7)
C70.0631 (7)0.3333 (8)0.4701 (6)0.082 (2)0.755 (7)
H7A0.11030.37780.39950.099*0.755 (7)
H7B0.07530.37600.53830.099*0.755 (7)
C80.0804 (6)0.3375 (8)0.4573 (7)0.111 (3)0.755 (7)
H8A0.09270.29050.39290.166*0.755 (7)
H8B0.11060.42480.44100.166*0.755 (7)
H8C0.12780.29990.53010.166*0.755 (7)
C6'0.129 (3)0.259 (3)0.478 (3)0.061 (7)0.245 (7)
H6'10.14630.31220.40290.073*0.245 (7)
H6'20.08750.31020.53890.073*0.245 (7)
C7'0.047 (2)0.145 (2)0.4661 (19)0.081 (6)0.245 (7)
H7'10.04510.08720.53890.097*0.245 (7)
H7'20.04010.17810.46060.097*0.245 (7)
C8'0.091 (2)0.069 (2)0.361 (2)0.106 (8)0.245 (7)
H8'10.06650.11520.28990.158*0.245 (7)
H8'20.05110.01220.37550.158*0.245 (7)
H8'30.18270.05490.35260.158*0.245 (7)
C90.0087 (3)0.3316 (3)0.8131 (3)0.0440 (8)
C100.0964 (3)0.4090 (3)0.8322 (3)0.0394 (7)
C110.0983 (3)0.5332 (3)0.8570 (3)0.0414 (7)
C120.0035 (3)0.6349 (3)0.8720 (3)0.0458 (8)
C130.2919 (3)0.4388 (3)0.8542 (3)0.0461 (8)
C140.4291 (18)0.4147 (17)0.8779 (12)0.053 (3)0.556 (13)
H14A0.45490.32550.87140.064*0.556 (13)
H14B0.43590.43240.95840.064*0.556 (13)
C150.5185 (8)0.5000 (8)0.7884 (11)0.072 (3)0.556 (13)
H15A0.49070.58890.79430.086*0.556 (13)
H15B0.60500.48830.80940.086*0.556 (13)
C160.5214 (18)0.472 (2)0.6607 (18)0.099 (7)0.556 (13)
H16A0.53810.38170.65610.149*0.556 (13)
H16B0.58790.51840.61040.149*0.556 (13)
H16C0.43980.49730.63460.149*0.556 (13)
C14'0.434 (2)0.435 (2)0.8282 (14)0.055 (4)0.444 (13)
H14C0.46710.34810.84670.066*0.444 (13)
H14D0.46740.48820.87990.066*0.444 (13)
C15'0.484 (2)0.481 (2)0.6993 (19)0.073 (6)0.444 (13)
H15C0.44400.43480.64670.087*0.444 (13)
H15D0.46140.57110.68310.087*0.444 (13)
C16'0.6296 (14)0.4600 (12)0.6737 (12)0.097 (5)0.444 (13)
H16D0.66940.49890.73040.146*0.444 (13)
H16E0.65940.49790.59460.146*0.444 (13)
H16F0.65170.36990.67990.146*0.444 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mg10.0463 (6)0.0375 (6)0.0393 (6)0.0013 (5)0.0014 (5)0.0057 (5)
N10.0440 (16)0.0449 (16)0.0392 (15)0.0004 (13)0.0037 (12)0.0055 (12)
N20.0598 (18)0.0601 (19)0.0335 (14)0.0063 (15)0.0045 (13)0.0041 (13)
N30.0397 (15)0.0359 (15)0.0455 (15)0.0011 (12)0.0020 (11)0.0077 (12)
N40.0455 (16)0.0369 (15)0.0544 (17)0.0044 (13)0.0001 (12)0.0136 (13)
O10.0561 (14)0.0522 (14)0.0338 (12)0.0090 (11)0.0037 (10)0.0042 (10)
O20.0467 (15)0.0847 (19)0.0490 (14)0.0051 (13)0.0072 (11)0.0112 (13)
O30.0505 (15)0.081 (2)0.0572 (15)0.0037 (14)0.0082 (12)0.0142 (15)
O40.0756 (18)0.0645 (17)0.0461 (15)0.0060 (14)0.0160 (12)0.0019 (12)
O50.0453 (13)0.0449 (14)0.0563 (14)0.0062 (11)0.0051 (10)0.0118 (11)
O60.0408 (14)0.0581 (16)0.0834 (18)0.0030 (12)0.0140 (12)0.0103 (14)
O70.0511 (15)0.0474 (15)0.0758 (17)0.0120 (12)0.0069 (12)0.0071 (14)
O80.0629 (16)0.0412 (14)0.0641 (16)0.0011 (12)0.0120 (12)0.0083 (12)
O90.0830 (18)0.0568 (16)0.0445 (14)0.0250 (14)0.0133 (12)0.0008 (12)
O100.0755 (18)0.0428 (15)0.0765 (17)0.0136 (13)0.0259 (14)0.0151 (13)
O110.087 (2)0.078 (2)0.098 (2)0.0325 (17)0.0461 (17)0.0259 (17)
O120.131 (3)0.138 (3)0.0634 (19)0.048 (2)0.0415 (19)0.021 (2)
O130.113 (3)0.090 (3)0.129 (3)0.003 (2)0.041 (2)0.056 (2)
O140.072 (3)0.060 (3)0.045 (3)0.006 (3)0.017 (2)0.006 (2)
C10.047 (2)0.0414 (19)0.0438 (19)0.0021 (15)0.0063 (15)0.0119 (15)
C20.0417 (18)0.0346 (17)0.0378 (17)0.0005 (14)0.0015 (13)0.0072 (13)
C30.0495 (19)0.0372 (18)0.0415 (18)0.0001 (15)0.0029 (15)0.0064 (14)
C40.056 (2)0.0393 (19)0.046 (2)0.0010 (16)0.0065 (17)0.0071 (15)
C50.055 (2)0.071 (3)0.044 (2)0.0056 (19)0.0095 (17)0.0099 (18)
C60.063 (5)0.076 (7)0.058 (4)0.007 (6)0.018 (3)0.006 (5)
C70.072 (4)0.091 (5)0.083 (4)0.003 (4)0.017 (3)0.003 (4)
C80.068 (4)0.132 (7)0.126 (6)0.010 (4)0.023 (4)0.013 (5)
C6'0.060 (15)0.064 (18)0.057 (12)0.005 (18)0.014 (10)0.002 (14)
C7'0.072 (14)0.095 (17)0.075 (13)0.001 (12)0.015 (11)0.001 (12)
C8'0.092 (15)0.117 (19)0.108 (17)0.004 (14)0.025 (13)0.001 (15)
C90.0417 (19)0.045 (2)0.0439 (18)0.0009 (16)0.0028 (14)0.0023 (15)
C100.0393 (17)0.0366 (18)0.0393 (17)0.0017 (14)0.0013 (13)0.0020 (14)
C110.0438 (18)0.0407 (19)0.0368 (17)0.0000 (15)0.0004 (13)0.0009 (14)
C120.055 (2)0.041 (2)0.0374 (18)0.0005 (16)0.0043 (15)0.0007 (15)
C130.0423 (18)0.0410 (19)0.055 (2)0.0019 (15)0.0004 (15)0.0118 (16)
C140.045 (5)0.055 (7)0.062 (8)0.005 (4)0.010 (7)0.015 (7)
C150.050 (5)0.064 (5)0.099 (8)0.012 (4)0.002 (5)0.015 (5)
C160.091 (19)0.097 (10)0.098 (13)0.009 (10)0.031 (9)0.015 (8)
C14'0.048 (6)0.049 (8)0.068 (11)0.004 (6)0.000 (10)0.016 (9)
C15'0.051 (10)0.070 (8)0.089 (17)0.006 (7)0.017 (10)0.015 (10)
C16'0.060 (9)0.090 (9)0.133 (11)0.005 (6)0.003 (7)0.003 (7)
Geometric parameters (Å, º) top
Mg1—O92.019 (2)C5—C6'1.51 (3)
Mg1—O102.055 (3)C6—C71.508 (11)
Mg1—O12.090 (2)C6—H6A0.9700
Mg1—O52.118 (2)C6—H6B0.9700
Mg1—N12.193 (3)C7—C81.535 (9)
Mg1—N32.226 (3)C7—H7A0.9700
N1—C51.325 (4)C7—H7B0.9700
N1—C21.365 (4)C8—H8A0.9600
N2—C51.349 (4)C8—H8B0.9600
N2—C31.370 (4)C8—H8C0.9600
N2—H20.8600C6'—C7'1.54 (3)
N3—C131.332 (4)C6'—H6'10.9700
N3—C101.369 (4)C6'—H6'20.9700
N4—C131.354 (4)C7'—C8'1.52 (3)
N4—C111.363 (4)C7'—H7'10.9700
N4—H40.8600C7'—H7'20.9700
O1—C11.252 (4)C8'—H8'10.9600
O2—C11.262 (4)C8'—H8'20.9600
O3—C41.303 (4)C8'—H8'30.9600
O3—H30.8200C9—C101.467 (5)
O4—C41.213 (4)C10—C111.372 (4)
O5—C91.246 (4)C11—C121.474 (5)
O6—C91.280 (4)C13—C14'1.48 (2)
O7—C121.285 (4)C13—C141.506 (19)
O7—H70.8200C14—C151.533 (17)
O8—C121.227 (4)C14—H14A0.9700
O9—H9C0.8500C14—H14B0.9700
O9—H9D0.8500C15—C161.52 (2)
O10—H10C0.8500C15—H15A0.9700
O10—H10D0.8500C15—H15B0.9700
O11—H11C0.8501C16—H16A0.9600
O11—H11D0.8500C16—H16B0.9600
O12—H12C0.8499C16—H16C0.9600
O12—H12D0.8499C14'—C15'1.52 (2)
O13—H13C0.8500C14'—H14C0.9700
O13—H13D0.8499C14'—H14D0.9700
O14—H14G0.8500C15'—C16'1.52 (2)
O14—H14H0.8500C15'—H15C0.9700
C1—C21.481 (4)C15'—H15D0.9700
C2—C31.374 (4)C16'—H16D0.9600
C3—C41.465 (5)C16'—H16E0.9600
C5—C61.500 (11)C16'—H16F0.9600
O9—Mg1—O1091.24 (11)C8—C7—H7B109.7
O9—Mg1—O193.24 (10)H7A—C7—H7B108.2
O10—Mg1—O194.26 (11)C5—C6'—C7'101.1 (19)
O9—Mg1—O592.42 (10)C5—C6'—H6'1111.6
O10—Mg1—O595.35 (11)C7'—C6'—H6'1111.6
O1—Mg1—O5168.73 (10)C5—C6'—H6'2111.6
O9—Mg1—N1170.33 (11)C7'—C6'—H6'2111.6
O10—Mg1—N187.42 (10)H6'1—C6'—H6'2109.4
O1—Mg1—N177.33 (9)C8'—C7'—C6'117 (2)
O5—Mg1—N197.24 (10)C8'—C7'—H7'1108.1
O9—Mg1—N389.86 (10)C6'—C7'—H7'1108.1
O10—Mg1—N3171.92 (12)C8'—C7'—H7'2108.1
O1—Mg1—N393.67 (10)C6'—C7'—H7'2108.1
O5—Mg1—N376.60 (9)H7'1—C7'—H7'2107.3
N1—Mg1—N392.82 (10)C7'—C8'—H8'1109.5
C5—N1—C2106.2 (3)C7'—C8'—H8'2109.5
C5—N1—Mg1144.1 (2)H8'1—C8'—H8'2109.5
C2—N1—Mg1109.73 (19)C7'—C8'—H8'3109.5
C5—N2—C3108.5 (3)H8'1—C8'—H8'3109.5
C5—N2—H2125.7H8'2—C8'—H8'3109.5
C3—N2—H2125.7O5—C9—O6123.0 (3)
C13—N3—C10105.7 (3)O5—C9—C10118.2 (3)
C13—N3—Mg1144.0 (2)O6—C9—C10118.8 (3)
C10—N3—Mg1109.6 (2)N3—C10—C11110.4 (3)
C13—N4—C11108.7 (3)N3—C10—C9117.6 (3)
C13—N4—H4125.6C11—C10—C9131.9 (3)
C11—N4—H4125.6N4—C11—C10105.0 (3)
C1—O1—Mg1118.6 (2)N4—C11—C12122.6 (3)
C4—O3—H3109.5C10—C11—C12132.3 (3)
C9—O5—Mg1117.5 (2)O8—C12—O7123.4 (3)
C12—O7—H7109.5O8—C12—C11120.1 (3)
Mg1—O9—H9C119.2O7—C12—C11116.5 (3)
Mg1—O9—H9D130.5N3—C13—N4110.1 (3)
H9C—O9—H9D108.5N3—C13—C14'125.5 (9)
Mg1—O10—H10C107.2N4—C13—C14'121.5 (9)
Mg1—O10—H10D140.1N3—C13—C14125.3 (7)
H10C—O10—H10D108.2N4—C13—C14124.0 (7)
H11C—O11—H11D108.6C13—C14—C15110.3 (9)
H12C—O12—H12D108.7C13—C14—H14A109.6
H13C—O13—H13D107.8C15—C14—H14A109.6
H14G—O14—H14H108.8C13—C14—H14B109.6
O1—C1—O2125.2 (3)C15—C14—H14B109.6
O1—C1—C2116.1 (3)H14A—C14—H14B108.1
O2—C1—C2118.6 (3)C16—C15—C14113.1 (11)
N1—C2—C3110.1 (3)C16—C15—H15A109.0
N1—C2—C1118.1 (3)C14—C15—H15A109.0
C3—C2—C1131.7 (3)C16—C15—H15B109.0
N2—C3—C2104.8 (3)C14—C15—H15B109.0
N2—C3—C4121.6 (3)H15A—C15—H15B107.8
C2—C3—C4133.5 (3)C13—C14'—C15'113.6 (16)
O4—C4—O3121.5 (3)C13—C14'—H14C108.9
O4—C4—C3121.4 (3)C15'—C14'—H14C108.9
O3—C4—C3117.1 (3)C13—C14'—H14D108.9
N1—C5—N2110.3 (3)C15'—C14'—H14D108.9
N1—C5—C6124.3 (5)H14C—C14'—H14D107.7
N2—C5—C6125.0 (5)C16'—C15'—C14'111 (2)
N1—C5—C6'126.9 (12)C16'—C15'—H15C109.3
N2—C5—C6'118.1 (12)C14'—C15'—H15C109.3
C5—C6—C7110.8 (7)C16'—C15'—H15D109.3
C5—C6—H6A109.5C14'—C15'—H15D109.3
C7—C6—H6A109.5H15C—C15'—H15D108.0
C5—C6—H6B109.5C15'—C16'—H16D109.5
C7—C6—H6B109.5C15'—C16'—H16E109.5
H6A—C6—H6B108.1H16D—C16'—H16E109.5
C6—C7—C8109.9 (6)C15'—C16'—H16F109.5
C6—C7—H7A109.7H16D—C16'—H16F109.5
C8—C7—H7A109.7H16E—C16'—H16F109.5
C6—C7—H7B109.7
O10—Mg1—N1—C579.7 (4)C2—N1—C5—C6'156.2 (14)
O1—Mg1—N1—C5174.6 (4)Mg1—N1—C5—C6'26.8 (15)
O5—Mg1—N1—C515.4 (4)C3—N2—C5—N11.0 (4)
N3—Mg1—N1—C592.2 (4)C3—N2—C5—C6172.1 (6)
O10—Mg1—N1—C297.2 (2)C3—N2—C5—C6'158.3 (13)
O1—Mg1—N1—C22.28 (19)N1—C5—C6—C797.0 (7)
O5—Mg1—N1—C2167.7 (2)N2—C5—C6—C790.8 (8)
N3—Mg1—N1—C290.9 (2)C6'—C5—C6—C78 (3)
O9—Mg1—N3—C1381.6 (4)C5—C6—C7—C8173.2 (6)
O1—Mg1—N3—C1311.7 (4)N1—C5—C6'—C7'100.8 (18)
O5—Mg1—N3—C13174.1 (4)N2—C5—C6'—C7'106.1 (17)
N1—Mg1—N3—C1389.1 (4)C6—C5—C6'—C7'6.8 (19)
O9—Mg1—N3—C1087.2 (2)C5—C6'—C7'—C8'70 (2)
O1—Mg1—N3—C10179.55 (19)Mg1—O5—C9—O6174.7 (2)
O5—Mg1—N3—C105.30 (19)Mg1—O5—C9—C105.3 (4)
N1—Mg1—N3—C10102.1 (2)C13—N3—C10—C110.2 (3)
O9—Mg1—O1—C1179.6 (2)Mg1—N3—C10—C11173.0 (2)
O10—Mg1—O1—C188.9 (2)C13—N3—C10—C9177.8 (3)
O5—Mg1—O1—C159.6 (6)Mg1—N3—C10—C94.6 (3)
N1—Mg1—O1—C12.5 (2)O5—C9—C10—N30.1 (4)
N3—Mg1—O1—C189.5 (2)O6—C9—C10—N3180.0 (3)
O9—Mg1—O5—C983.4 (2)O5—C9—C10—C11177.1 (3)
O10—Mg1—O5—C9174.8 (2)O6—C9—C10—C112.9 (5)
O1—Mg1—O5—C936.7 (6)C13—N4—C11—C100.3 (3)
N1—Mg1—O5—C997.1 (2)C13—N4—C11—C12178.3 (3)
N3—Mg1—O5—C95.9 (2)N3—C10—C11—N40.3 (3)
Mg1—O1—C1—O2177.7 (3)C9—C10—C11—N4177.5 (3)
Mg1—O1—C1—C22.2 (4)N3—C10—C11—C12178.1 (3)
C5—N1—C2—C31.2 (4)C9—C10—C11—C120.9 (6)
Mg1—N1—C2—C3179.3 (2)N4—C11—C12—O80.3 (5)
C5—N1—C2—C1176.1 (3)C10—C11—C12—O8178.4 (3)
Mg1—N1—C2—C12.0 (3)N4—C11—C12—O7179.3 (3)
O1—C1—C2—N10.0 (4)C10—C11—C12—O71.1 (5)
O2—C1—C2—N1180.0 (3)C10—N3—C13—N40.0 (4)
O1—C1—C2—C3176.7 (3)Mg1—N3—C13—N4169.0 (3)
O2—C1—C2—C33.4 (5)C10—N3—C13—C14'161.0 (8)
C5—N2—C3—C20.2 (4)Mg1—N3—C13—C14'29.9 (9)
C5—N2—C3—C4177.5 (3)C10—N3—C13—C14171.5 (7)
N1—C2—C3—N20.6 (3)Mg1—N3—C13—C142.5 (8)
C1—C2—C3—N2176.2 (3)C11—N4—C13—N30.2 (4)
N1—C2—C3—C4178.0 (3)C11—N4—C13—C14'162.1 (8)
C1—C2—C3—C41.1 (6)C11—N4—C13—C14171.5 (7)
N2—C3—C4—O40.9 (5)N3—C13—C14—C15122.3 (10)
C2—C3—C4—O4177.9 (3)N4—C13—C14—C1567.3 (11)
N2—C3—C4—O3178.4 (3)C14'—C13—C14—C1524 (3)
C2—C3—C4—O31.4 (6)C13—C14—C15—C1663.5 (15)
C2—N1—C5—N21.4 (4)N3—C13—C14'—C15'81.0 (19)
Mg1—N1—C5—N2178.4 (3)N4—C13—C14'—C15'78.0 (18)
C2—N1—C5—C6171.8 (6)C14—C13—C14'—C15'179 (5)
Mg1—N1—C5—C65.2 (8)C13—C14'—C15'—C16'173.1 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O120.861.892.745 (4)170
N4—H4···O130.861.912.737 (4)162
O3—H3···O20.821.702.511 (3)173
O7—H7···O60.821.652.461 (3)172
O9—H9C···O8i0.851.882.732 (3)177
O9—H9D···O11ii0.851.832.678 (4)176
O10—H10C···O4iii0.851.942.787 (3)174
O10—H10D···O8iv0.852.062.905 (3)174
O11—H11C···O2v0.851.952.794 (3)172
O11—H11D···O5vi0.852.052.893 (3)172
O12—H12C···O7vi0.852.052.888 (4)167
O12—H12D···O14v0.851.842.672 (6)167
O13—H13C···O140.851.852.643 (6)156
O13—H13D···O11vii0.852.072.869 (5)156
O14—H14G···O1viii0.852.002.816 (5)162
O14—H14H···O1ix0.851.982.799 (5)162
Symmetry codes: (i) x, y+1, z+2; (ii) x, y1, z+1; (iii) x+1, y, z+1; (iv) x, y1, z; (v) x+1, y+1, z+1; (vi) x, y+1, z+1; (vii) x, y, z+1; (viii) x, y+1, z; (ix) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula[Mg(C8H9N2O4)2(H2O)2]·3.5H2O
Mr517.74
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.516 (1), 10.5332 (11), 11.3989 (13)
α, β, γ (°)83.288 (1), 81.783 (1), 86.458 (2)
V3)1239.8 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.48 × 0.38 × 0.35
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.935, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
6478, 4321, 2780
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.178, 1.00
No. of reflections4321
No. of parameters378
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.31

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O120.861.892.745 (4)170
N4—H4···O130.861.912.737 (4)162
O3—H3···O20.821.702.511 (3)173
O7—H7···O60.821.652.461 (3)172
O9—H9C···O8i0.851.882.732 (3)177
O9—H9D···O11ii0.851.832.678 (4)176
O10—H10C···O4iii0.851.942.787 (3)174
O10—H10D···O8iv0.852.062.905 (3)174
O11—H11C···O2v0.851.952.794 (3)172
O11—H11D···O5vi0.852.052.893 (3)172
O12—H12C···O7vi0.852.052.888 (4)167
O12—H12D···O14v0.851.842.672 (6)167
O13—H13C···O140.851.852.643 (6)156
O13—H13D···O11vii0.852.072.869 (5)156
O14—H14G···O1viii0.852.002.816 (5)162
O14—H14H···O1ix0.851.982.799 (5)162
Symmetry codes: (i) x, y+1, z+2; (ii) x, y1, z+1; (iii) x+1, y, z+1; (iv) x, y1, z; (v) x+1, y+1, z+1; (vi) x, y+1, z+1; (vii) x, y, z+1; (viii) x, y+1, z; (ix) x+1, y+1, z+2.
 

Acknowledgements

The authors thank Henan University of Urban Construction.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSengupta, P., Dinda, R., Ghosh, S. & Sheldrick, W. S. (2001). Polyhedron, 20, 3349–3354.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSong, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWang, C.-F., Gao, E.-Q., Zheng, H. & Yan, C.-H. (2004). Chem. Commun. pp. 720–721.  Web of Science CSD CrossRef Google Scholar
First citationYan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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