Diaqua-bis(2-methyl-1H-imidazol-3-ium-4,5-dicarboxyl-ato-κO,O')magnesium.

The title compound, [Mg(C(6)H(5)N(2)O(4))(2)(H(2)O)(2)], was prepared by reaction of Mg(NO(3))(2) and 2-methyl-1H-imidazole-4,5-dicarboxylic acid under hydro-thermal conditions. The Mg(II) atom lies on an inversion centre and displays a distorted octa-hedral coordination geometry. An extended three-dimensional network of inter-molecular O-H⋯O and N-H⋯O hydrogen bonds stabilizes the crystal structure.

Related literature

For the crystal structures of metal complexes with N-heterocyclic carboxylic acids, see: Nie et al. (2007 ▶); Liang et al. (2002 ▶); Net et al. (1989 ▶); Zeng et al. (2008 ▶).

Experimental

Crystal data

[Mg(C6H5N2O4)2(H2O)2]

M = 398.58

Triclinic,

a = 4.943 (2) Å

b = 8.750 (6) Å

c = 9.621 (6) Å

α = 109.18 (3)°

β = 95.142 (17)°

γ = 93.14 (2)°

V = 389.9 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.18 mm−1

T = 292 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.948, T max = 0.967

4002 measured reflections

1767 independent reflections

1308 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.213

S = 1.19

1767 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902176X/rz2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902176X/rz2332Isup2.hkl

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

[Mg(C6H5N2O4)2(H2O)2]	Z = 1
Mr = 398.58	F(000) = 206
Triclinic, P1	Dx = 1.698 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.943 (2) Å	Cell parameters from 1023 reflections
b = 8.750 (6) Å	θ = 3.9–27.4°
c = 9.621 (6) Å	µ = 0.18 mm−1
α = 109.18 (3)°	T = 292 K
β = 95.142 (17)°	Block, colourless
γ = 93.14 (2)°	0.30 × 0.25 × 0.20 mm
V = 389.9 (4) Å3

Rigaku SCXmini diffractometer	1767 independent reflections
Radiation source: fine-focus sealed tube	1308 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 2.7°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.948, Tmax = 0.967	l = −12→12
4002 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.1078P)2 + 0.1465P] where P = (Fo2 + 2Fc2)/3
1767 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.42 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
Mg1	0.5000	1.0000	1.0000	0.0250 (4)
C1	0.3793 (6)	0.7562 (4)	0.6015 (3)	0.0229 (7)
C2	0.5912 (6)	0.8628 (4)	0.6010 (3)	0.0223 (7)
C3	0.5089 (7)	0.6811 (4)	0.3730 (4)	0.0267 (7)
C4	0.5167 (9)	0.5941 (5)	0.2137 (4)	0.0385 (9)
H4A	0.4178	0.6492	0.1569	0.058*
H4B	0.4347	0.4851	0.1885	0.058*
H4C	0.7026	0.5915	0.1922	0.058*
C5	0.1991 (7)	0.7356 (4)	0.7122 (3)	0.0240 (7)
C6	0.7466 (6)	1.0094 (4)	0.7140 (3)	0.0233 (7)
N1	0.3343 (6)	0.6454 (3)	0.4585 (3)	0.0268 (6)
H1	0.2007	0.5554	0.4365	0.040*
N2	0.6676 (6)	0.8120 (3)	0.4581 (3)	0.0258 (6)
H2	0.7914	0.8719	0.4213	0.039*
O1	0.6722 (5)	1.0584 (3)	0.8405 (2)	0.0319 (6)
O2	0.9380 (5)	1.0749 (3)	0.6734 (3)	0.0380 (7)
O3	0.2358 (5)	0.8310 (3)	0.8427 (2)	0.0312 (6)
O4	0.0166 (6)	0.6225 (3)	0.6638 (3)	0.0410 (7)
O5	0.2236 (5)	1.1757 (3)	1.0012 (3)	0.0336 (6)
H5B	0.1354	1.1572	0.9070	0.050*
H5A	0.0940	1.1836	1.0574	0.050*

	U11	U22	U33	U12	U13	U23
Mg1	0.0230 (8)	0.0287 (8)	0.0195 (8)	−0.0077 (6)	0.0050 (6)	0.0042 (6)
C1	0.0240 (15)	0.0222 (15)	0.0209 (15)	−0.0021 (12)	0.0033 (12)	0.0055 (12)
C2	0.0213 (14)	0.0243 (15)	0.0216 (15)	−0.0001 (12)	0.0050 (12)	0.0078 (12)
C3	0.0294 (17)	0.0240 (16)	0.0261 (16)	−0.0019 (13)	0.0057 (13)	0.0076 (13)
C4	0.054 (2)	0.0332 (19)	0.0227 (18)	−0.0042 (17)	0.0105 (16)	0.0014 (15)
C5	0.0232 (15)	0.0254 (15)	0.0224 (15)	−0.0035 (12)	0.0057 (12)	0.0067 (12)
C6	0.0230 (15)	0.0259 (16)	0.0206 (15)	−0.0033 (12)	0.0031 (12)	0.0081 (13)
N1	0.0277 (14)	0.0253 (14)	0.0248 (14)	−0.0064 (11)	0.0068 (11)	0.0052 (11)
N2	0.0284 (14)	0.0268 (14)	0.0228 (14)	−0.0031 (11)	0.0060 (11)	0.0092 (11)
O1	0.0353 (13)	0.0336 (14)	0.0227 (12)	−0.0103 (11)	0.0076 (10)	0.0049 (10)
O2	0.0346 (14)	0.0432 (16)	0.0330 (14)	−0.0165 (12)	0.0112 (11)	0.0098 (12)
O3	0.0319 (13)	0.0347 (14)	0.0208 (12)	−0.0114 (10)	0.0069 (10)	0.0022 (10)
O4	0.0408 (15)	0.0392 (15)	0.0323 (14)	−0.0239 (12)	0.0092 (12)	0.0008 (11)
O5	0.0280 (13)	0.0385 (14)	0.0326 (13)	−0.0015 (10)	0.0091 (10)	0.0090 (11)

Mg1—O1i	2.010 (2)	C3—C4	1.475 (5)
Mg1—O1	2.010 (2)	C4—H4A	0.9600
Mg1—O3i	2.036 (2)	C4—H4B	0.9600
Mg1—O3	2.036 (2)	C4—H4C	0.9600
Mg1—O5i	2.110 (3)	C5—O4	1.238 (4)
Mg1—O5	2.110 (3)	C5—O3	1.249 (4)
C1—C2	1.365 (4)	C6—O2	1.237 (4)
C1—N1	1.388 (4)	C6—O1	1.247 (4)
C1—C5	1.496 (4)	N1—H1	0.9534
C2—N2	1.393 (4)	N2—H2	0.9489
C2—C6	1.498 (5)	O5—H5B	0.9297
C3—N2	1.330 (4)	O5—H5A	0.8656
C3—N1	1.336 (4)
O1i—Mg1—O1	180.000 (1)	C3—C4—H4A	109.5
O1i—Mg1—O3i	89.92 (10)	C3—C4—H4B	109.5
O1—Mg1—O3i	90.08 (10)	H4A—C4—H4B	109.5
O1i—Mg1—O3	90.08 (10)	C3—C4—H4C	109.5
O1—Mg1—O3	89.92 (10)	H4A—C4—H4C	109.5
O3i—Mg1—O3	180.000 (1)	H4B—C4—H4C	109.5
O1i—Mg1—O5i	87.90 (11)	O4—C5—O3	124.6 (3)
O1—Mg1—O5i	92.10 (11)	O4—C5—C1	115.5 (3)
O3i—Mg1—O5i	88.95 (11)	O3—C5—C1	119.9 (3)
O3—Mg1—O5i	91.05 (11)	O2—C6—O1	124.7 (3)
O1i—Mg1—O5	92.10 (11)	O2—C6—C2	117.0 (3)
O1—Mg1—O5	87.90 (11)	O1—C6—C2	118.3 (3)
O3i—Mg1—O5	91.05 (11)	C3—N1—C1	110.7 (3)
O3—Mg1—O5	88.95 (11)	C3—N1—H1	129.8
O5i—Mg1—O5	180.000 (1)	C1—N1—H1	119.3
C2—C1—N1	105.8 (3)	C3—N2—C2	110.1 (3)
C2—C1—C5	136.3 (3)	C3—N2—H2	123.8
N1—C1—C5	117.9 (3)	C2—N2—H2	125.2
C1—C2—N2	106.6 (3)	C6—O1—Mg1	147.0 (2)
C1—C2—C6	135.2 (3)	C5—O3—Mg1	145.7 (2)
N2—C2—C6	118.2 (3)	Mg1—O5—H5B	111.2
N2—C3—N1	106.8 (3)	Mg1—O5—H5A	117.4
N2—C3—C4	127.0 (3)	H5B—O5—H5A	104.9
N1—C3—C4	126.2 (3)
N1—C1—C2—N2	−0.3 (4)	N1—C3—N2—C2	−0.7 (4)
C5—C1—C2—N2	−179.6 (4)	C4—C3—N2—C2	177.5 (4)
N1—C1—C2—C6	−179.5 (3)	C1—C2—N2—C3	0.7 (4)
C5—C1—C2—C6	1.2 (7)	C6—C2—N2—C3	−180.0 (3)
C2—C1—C5—O4	176.8 (4)	O2—C6—O1—Mg1	−150.7 (3)
N1—C1—C5—O4	−2.4 (5)	C2—C6—O1—Mg1	30.6 (6)
C2—C1—C5—O3	−2.0 (6)	O3i—Mg1—O1—C6	142.4 (4)
N1—C1—C5—O3	178.8 (3)	O3—Mg1—O1—C6	−37.6 (4)
C1—C2—C6—O2	177.8 (4)	O5i—Mg1—O1—C6	53.4 (4)
N2—C2—C6—O2	−1.3 (5)	O5—Mg1—O1—C6	−126.6 (4)
C1—C2—C6—O1	−3.4 (6)	O4—C5—O3—Mg1	163.9 (3)
N2—C2—C6—O1	177.5 (3)	C1—C5—O3—Mg1	−17.4 (6)
N2—C3—N1—C1	0.5 (4)	O1i—Mg1—O3—C5	−151.8 (4)
C4—C3—N1—C1	−177.8 (3)	O1—Mg1—O3—C5	28.2 (4)
C2—C1—N1—C3	−0.1 (4)	O5i—Mg1—O3—C5	−63.9 (4)
C5—C1—N1—C3	179.3 (3)	O5—Mg1—O3—C5	116.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ii	0.95	1.78	2.696 (4)	161
N2—H2···O2iii	0.95	1.81	2.727 (4)	162
O5—H5B···O2iv	0.93	2.23	3.155 (4)	172
O5—H5B···O1iv	0.93	2.36	2.961 (4)	122
O5—H5A···O3v	0.87	1.98	2.841 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.95	1.78	2.696 (4)	161
N2—H2⋯O2ii	0.95	1.81	2.727 (4)	162
O5—H5B⋯O2iii	0.93	2.23	3.155 (4)	172
O5—H5B⋯O1iii	0.93	2.36	2.961 (4)	122
O5—H5A⋯O3iv	0.87	1.98	2.841 (4)	170

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