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

Liu, X.-Y.; Liu, L.-H.

doi:10.1107/S1600536810005684

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m305

doi:10.1107/S1600536810005684

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

Xiang-Yun Liu ^a ^* and Li-Hua Liu ^a

^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 Mg^II 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 ); Song et al. (2010 ); Wang et al. (2004 ); Yan et al. (2010 ).

Experimental

Crystal data

[Mg(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O
M_r = 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 ) T_min = 0.935, T_max = 0.952
6478 measured reflections
4321 independent reflections
2780 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.178
S = 1.00
4321 reflections
378 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O8^iv	0.85	2.06	2.905 (3)	174
O11—H11C⋯O2^v	0.85	1.95	2.794 (3)	172
O11—H11D⋯O5^vi	0.85	2.05	2.893 (3)	172
O12—H12C⋯O7^vi	0.85	2.05	2.888 (4)	167
O12—H12D⋯O14^v	0.85	1.84	2.672 (6)	167
O13—H13C⋯O14	0.85	1.85	2.643 (6)	156
O13—H13D⋯O11^vii	0.85	2.07	2.869 (5)	156
O14—H14G⋯O1^viii	0.85	2.00	2.816 (5)	162
O14—H14H⋯O1^ix	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S1600536810005684/hy2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005684/hy2281Isup2.hkl

checkCIF report

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 Mg^II complex.

As illustrated in Fig. 1, the title complex molecule contains one Mg^II 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.

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

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
	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]·3.5H₂O	Z = 2
M_r = 517.74	F(000) = 546
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.516 (1) Å	Cell parameters from 2051 reflections
b = 10.5332 (11) Å	θ = 2.5–23.9°
c = 11.3989 (13) Å	µ = 0.14 mm⁻¹
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 tube	2780 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.935, T_max = 0.952	k = −7→12
6478 measured reflections	l = −12→13

Refinement top

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0865P)² + 0.6255P] where P = (F_o² + 2F_c²)/3
4321 reflections	(Δ/σ)_max = 0.001
378 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Mg(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O	γ = 86.458 (2)°
M_r = 517.74	V = 1239.8 (2) Å³
Triclinic, P1	Z = 2
a = 10.516 (1) Å	Mo Kα radiation
b = 10.5332 (11) Å	µ = 0.14 mm⁻¹
c = 11.3989 (13) Å	T = 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)
T_min = 0.935, T_max = 0.952	R_int = 0.028
6478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
4321 reflections	Δρ_min = −0.31 e Å⁻³
378 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mg1	0.20602 (10)	0.14342 (10)	0.81297 (9)	0.0417 (3)
N1	0.2821 (2)	0.1678 (3)	0.6227 (2)	0.0429 (6)
N2	0.3556 (3)	0.1891 (3)	0.4316 (2)	0.0518 (7)
H2	0.3565	0.2023	0.3556	0.062*
N3	0.2165 (2)	0.3506 (2)	0.8307 (2)	0.0406 (6)
N4	0.2228 (2)	0.5498 (3)	0.8701 (2)	0.0455 (7)
H4	0.2525	0.6192	0.8859	0.055*
O1	0.4034 (2)	0.1060 (2)	0.81403 (18)	0.0481 (6)
O2	0.5972 (2)	0.1009 (3)	0.7049 (2)	0.0601 (7)
O3	0.6855 (2)	0.1268 (3)	0.4872 (2)	0.0639 (7)
H3	0.6563	0.1120	0.5578	0.096*
O4	0.6100 (2)	0.1666 (2)	0.3161 (2)	0.0652 (7)
O5	0.0167 (2)	0.2175 (2)	0.7964 (2)	0.0483 (6)
O6	−0.1219 (2)	0.3840 (2)	0.8141 (2)	0.0602 (7)
O7	−0.1173 (2)	0.6067 (2)	0.8584 (2)	0.0588 (7)
H7	−0.1178	0.5304	0.8504	0.088*
O8	0.0222 (2)	0.7397 (2)	0.8968 (2)	0.0580 (7)
O9	0.1655 (3)	0.1075 (2)	0.9919 (2)	0.0653 (8)
H9C	0.1071	0.1529	1.0290	0.078*
H9D	0.1832	0.0418	1.0385	0.078*
O10	0.1704 (3)	−0.0415 (2)	0.7915 (2)	0.0674 (8)
H10C	0.2394	−0.0744	0.7569	0.081*
H10D	0.1228	−0.1018	0.8241	0.081*
O11	0.2291 (3)	0.8974 (3)	0.1314 (3)	0.0858 (10)
H11C	0.2762	0.8940	0.1864	0.103*
H11D	0.1592	0.8619	0.1597	0.103*
O12	0.3299 (3)	0.2189 (4)	0.1936 (3)	0.1094 (13)
H12C	0.2705	0.2676	0.1671	0.131*
H12D	0.3729	0.1839	0.1359	0.131*
O13	0.3434 (3)	0.7359 (3)	0.9551 (3)	0.1053 (12)
H13C	0.4103	0.7795	0.9419	0.126*
H13D	0.2914	0.7684	1.0088	0.126*
O14	0.5130 (5)	0.9089 (5)	0.9622 (4)	0.0584 (13)	0.50
H14G	0.4816	0.9784	0.9298	0.070*	0.50
H14H	0.5333	0.9220	1.0292	0.070*	0.50
C1	0.4763 (3)	0.1168 (3)	0.7168 (3)	0.0438 (8)
C2	0.4130 (3)	0.1509 (3)	0.6087 (3)	0.0382 (7)
C3	0.4614 (3)	0.1646 (3)	0.4896 (3)	0.0430 (8)
C4	0.5913 (3)	0.1533 (3)	0.4242 (3)	0.0482 (8)
C5	0.2496 (3)	0.1891 (4)	0.5137 (3)	0.0563 (10)
C6	0.1138 (11)	0.1962 (10)	0.4864 (9)	0.064 (2)	0.755 (7)
H6A	0.0598	0.1492	0.5511	0.077*	0.755 (7)
H6B	0.1108	0.1566	0.4142	0.077*	0.755 (7)
C7	0.0631 (7)	0.3333 (8)	0.4701 (6)	0.082 (2)	0.755 (7)
H7A	0.1103	0.3778	0.3995	0.099*	0.755 (7)
H7B	0.0753	0.3760	0.5383	0.099*	0.755 (7)
C8	−0.0804 (6)	0.3375 (8)	0.4573 (7)	0.111 (3)	0.755 (7)
H8A	−0.0927	0.2905	0.3929	0.166*	0.755 (7)
H8B	−0.1106	0.4248	0.4410	0.166*	0.755 (7)
H8C	−0.1278	0.2999	0.5301	0.166*	0.755 (7)
C6'	0.129 (3)	0.259 (3)	0.478 (3)	0.061 (7)	0.245 (7)
H6'1	0.1463	0.3122	0.4029	0.073*	0.245 (7)
H6'2	0.0875	0.3102	0.5389	0.073*	0.245 (7)
C7'	0.047 (2)	0.145 (2)	0.4661 (19)	0.081 (6)	0.245 (7)
H7'1	0.0451	0.0872	0.5389	0.097*	0.245 (7)
H7'2	−0.0401	0.1781	0.4606	0.097*	0.245 (7)
C8'	0.091 (2)	0.069 (2)	0.361 (2)	0.106 (8)	0.245 (7)
H8'1	0.0665	0.1152	0.2899	0.158*	0.245 (7)
H8'2	0.0511	−0.0122	0.3755	0.158*	0.245 (7)
H8'3	0.1827	0.0549	0.3526	0.158*	0.245 (7)
C9	−0.0087 (3)	0.3316 (3)	0.8131 (3)	0.0440 (8)
C10	0.0964 (3)	0.4090 (3)	0.8322 (3)	0.0394 (7)
C11	0.0983 (3)	0.5332 (3)	0.8570 (3)	0.0414 (7)
C12	−0.0035 (3)	0.6349 (3)	0.8720 (3)	0.0458 (8)
C13	0.2919 (3)	0.4388 (3)	0.8542 (3)	0.0461 (8)
C14	0.4291 (18)	0.4147 (17)	0.8779 (12)	0.053 (3)	0.556 (13)
H14A	0.4549	0.3255	0.8714	0.064*	0.556 (13)
H14B	0.4359	0.4324	0.9584	0.064*	0.556 (13)
C15	0.5185 (8)	0.5000 (8)	0.7884 (11)	0.072 (3)	0.556 (13)
H15A	0.4907	0.5889	0.7943	0.086*	0.556 (13)
H15B	0.6050	0.4883	0.8094	0.086*	0.556 (13)
C16	0.5214 (18)	0.472 (2)	0.6607 (18)	0.099 (7)	0.556 (13)
H16A	0.5381	0.3817	0.6561	0.149*	0.556 (13)
H16B	0.5879	0.5184	0.6104	0.149*	0.556 (13)
H16C	0.4398	0.4973	0.6346	0.149*	0.556 (13)
C14'	0.434 (2)	0.435 (2)	0.8282 (14)	0.055 (4)	0.444 (13)
H14C	0.4671	0.3481	0.8467	0.066*	0.444 (13)
H14D	0.4674	0.4882	0.8799	0.066*	0.444 (13)
C15'	0.484 (2)	0.481 (2)	0.6993 (19)	0.073 (6)	0.444 (13)
H15C	0.4440	0.4348	0.6467	0.087*	0.444 (13)
H15D	0.4614	0.5711	0.6831	0.087*	0.444 (13)
C16'	0.6296 (14)	0.4600 (12)	0.6737 (12)	0.097 (5)	0.444 (13)
H16D	0.6694	0.4989	0.7304	0.146*	0.444 (13)
H16E	0.6594	0.4979	0.5946	0.146*	0.444 (13)
H16F	0.6517	0.3699	0.6799	0.146*	0.444 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg1	0.0463 (6)	0.0375 (6)	0.0393 (6)	0.0013 (5)	0.0014 (5)	−0.0057 (5)
N1	0.0440 (16)	0.0449 (16)	0.0392 (15)	0.0004 (13)	−0.0037 (12)	−0.0055 (12)
N2	0.0598 (18)	0.0601 (19)	0.0335 (14)	0.0063 (15)	−0.0045 (13)	−0.0041 (13)
N3	0.0397 (15)	0.0359 (15)	0.0455 (15)	0.0011 (12)	−0.0020 (11)	−0.0077 (12)
N4	0.0455 (16)	0.0369 (15)	0.0544 (17)	−0.0044 (13)	0.0001 (12)	−0.0136 (13)
O1	0.0561 (14)	0.0522 (14)	0.0338 (12)	0.0090 (11)	−0.0037 (10)	−0.0042 (10)
O2	0.0467 (15)	0.0847 (19)	0.0490 (14)	0.0051 (13)	−0.0072 (11)	−0.0112 (13)
O3	0.0505 (15)	0.081 (2)	0.0572 (15)	−0.0037 (14)	0.0082 (12)	−0.0142 (15)
O4	0.0756 (18)	0.0645 (17)	0.0461 (15)	0.0060 (14)	0.0160 (12)	−0.0019 (12)
O5	0.0453 (13)	0.0449 (14)	0.0563 (14)	−0.0062 (11)	−0.0051 (10)	−0.0118 (11)
O6	0.0408 (14)	0.0581 (16)	0.0834 (18)	0.0030 (12)	−0.0140 (12)	−0.0103 (14)
O7	0.0511 (15)	0.0474 (15)	0.0758 (17)	0.0120 (12)	−0.0069 (12)	−0.0071 (14)
O8	0.0629 (16)	0.0412 (14)	0.0641 (16)	0.0011 (12)	0.0120 (12)	−0.0083 (12)
O9	0.0830 (18)	0.0568 (16)	0.0445 (14)	0.0250 (14)	0.0133 (12)	0.0008 (12)
O10	0.0755 (18)	0.0428 (15)	0.0765 (17)	−0.0136 (13)	0.0259 (14)	−0.0151 (13)
O11	0.087 (2)	0.078 (2)	0.098 (2)	−0.0325 (17)	−0.0461 (17)	0.0259 (17)
O12	0.131 (3)	0.138 (3)	0.0634 (19)	0.048 (2)	−0.0415 (19)	−0.021 (2)
O13	0.113 (3)	0.090 (3)	0.129 (3)	0.003 (2)	−0.041 (2)	−0.056 (2)
O14	0.072 (3)	0.060 (3)	0.045 (3)	0.006 (3)	−0.017 (2)	−0.006 (2)
C1	0.047 (2)	0.0414 (19)	0.0438 (19)	0.0021 (15)	−0.0063 (15)	−0.0119 (15)
C2	0.0417 (18)	0.0346 (17)	0.0378 (17)	0.0005 (14)	−0.0015 (13)	−0.0072 (13)
C3	0.0495 (19)	0.0372 (18)	0.0415 (18)	−0.0001 (15)	−0.0029 (15)	−0.0064 (14)
C4	0.056 (2)	0.0393 (19)	0.046 (2)	−0.0010 (16)	0.0065 (17)	−0.0071 (15)
C5	0.055 (2)	0.071 (3)	0.044 (2)	0.0056 (19)	−0.0095 (17)	−0.0099 (18)
C6	0.063 (5)	0.076 (7)	0.058 (4)	−0.007 (6)	−0.018 (3)	−0.006 (5)
C7	0.072 (4)	0.091 (5)	0.083 (4)	0.003 (4)	−0.017 (3)	0.003 (4)
C8	0.068 (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)
C9	0.0417 (19)	0.045 (2)	0.0439 (18)	−0.0009 (16)	−0.0028 (14)	−0.0023 (15)
C10	0.0393 (17)	0.0366 (18)	0.0393 (17)	0.0017 (14)	0.0013 (13)	−0.0020 (14)
C11	0.0438 (18)	0.0407 (19)	0.0368 (17)	0.0000 (15)	0.0004 (13)	−0.0009 (14)
C12	0.055 (2)	0.041 (2)	0.0374 (18)	0.0005 (16)	0.0043 (15)	0.0007 (15)
C13	0.0423 (18)	0.0410 (19)	0.055 (2)	−0.0019 (15)	0.0004 (15)	−0.0118 (16)
C14	0.045 (5)	0.055 (7)	0.062 (8)	−0.005 (4)	−0.010 (7)	−0.015 (7)
C15	0.050 (5)	0.064 (5)	0.099 (8)	−0.012 (4)	0.002 (5)	−0.015 (5)
C16	0.091 (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—O9	2.019 (2)	C5—C6'	1.51 (3)
Mg1—O10	2.055 (3)	C6—C7	1.508 (11)
Mg1—O1	2.090 (2)	C6—H6A	0.9700
Mg1—O5	2.118 (2)	C6—H6B	0.9700
Mg1—N1	2.193 (3)	C7—C8	1.535 (9)
Mg1—N3	2.226 (3)	C7—H7A	0.9700
N1—C5	1.325 (4)	C7—H7B	0.9700
N1—C2	1.365 (4)	C8—H8A	0.9600
N2—C5	1.349 (4)	C8—H8B	0.9600
N2—C3	1.370 (4)	C8—H8C	0.9600
N2—H2	0.8600	C6'—C7'	1.54 (3)
N3—C13	1.332 (4)	C6'—H6'1	0.9700
N3—C10	1.369 (4)	C6'—H6'2	0.9700
N4—C13	1.354 (4)	C7'—C8'	1.52 (3)
N4—C11	1.363 (4)	C7'—H7'1	0.9700
N4—H4	0.8600	C7'—H7'2	0.9700
O1—C1	1.252 (4)	C8'—H8'1	0.9600
O2—C1	1.262 (4)	C8'—H8'2	0.9600
O3—C4	1.303 (4)	C8'—H8'3	0.9600
O3—H3	0.8200	C9—C10	1.467 (5)
O4—C4	1.213 (4)	C10—C11	1.372 (4)
O5—C9	1.246 (4)	C11—C12	1.474 (5)
O6—C9	1.280 (4)	C13—C14'	1.48 (2)
O7—C12	1.285 (4)	C13—C14	1.506 (19)
O7—H7	0.8200	C14—C15	1.533 (17)
O8—C12	1.227 (4)	C14—H14A	0.9700
O9—H9C	0.8500	C14—H14B	0.9700
O9—H9D	0.8500	C15—C16	1.52 (2)
O10—H10C	0.8500	C15—H15A	0.9700
O10—H10D	0.8500	C15—H15B	0.9700
O11—H11C	0.8501	C16—H16A	0.9600
O11—H11D	0.8500	C16—H16B	0.9600
O12—H12C	0.8499	C16—H16C	0.9600
O12—H12D	0.8499	C14'—C15'	1.52 (2)
O13—H13C	0.8500	C14'—H14C	0.9700
O13—H13D	0.8499	C14'—H14D	0.9700
O14—H14G	0.8500	C15'—C16'	1.52 (2)
O14—H14H	0.8500	C15'—H15C	0.9700
C1—C2	1.481 (4)	C15'—H15D	0.9700
C2—C3	1.374 (4)	C16'—H16D	0.9600
C3—C4	1.465 (5)	C16'—H16E	0.9600
C5—C6	1.500 (11)	C16'—H16F	0.9600

O9—Mg1—O10	91.24 (11)	C8—C7—H7B	109.7
O9—Mg1—O1	93.24 (10)	H7A—C7—H7B	108.2
O10—Mg1—O1	94.26 (11)	C5—C6'—C7'	101.1 (19)
O9—Mg1—O5	92.42 (10)	C5—C6'—H6'1	111.6
O10—Mg1—O5	95.35 (11)	C7'—C6'—H6'1	111.6
O1—Mg1—O5	168.73 (10)	C5—C6'—H6'2	111.6
O9—Mg1—N1	170.33 (11)	C7'—C6'—H6'2	111.6
O10—Mg1—N1	87.42 (10)	H6'1—C6'—H6'2	109.4
O1—Mg1—N1	77.33 (9)	C8'—C7'—C6'	117 (2)
O5—Mg1—N1	97.24 (10)	C8'—C7'—H7'1	108.1
O9—Mg1—N3	89.86 (10)	C6'—C7'—H7'1	108.1
O10—Mg1—N3	171.92 (12)	C8'—C7'—H7'2	108.1
O1—Mg1—N3	93.67 (10)	C6'—C7'—H7'2	108.1
O5—Mg1—N3	76.60 (9)	H7'1—C7'—H7'2	107.3
N1—Mg1—N3	92.82 (10)	C7'—C8'—H8'1	109.5
C5—N1—C2	106.2 (3)	C7'—C8'—H8'2	109.5
C5—N1—Mg1	144.1 (2)	H8'1—C8'—H8'2	109.5
C2—N1—Mg1	109.73 (19)	C7'—C8'—H8'3	109.5
C5—N2—C3	108.5 (3)	H8'1—C8'—H8'3	109.5
C5—N2—H2	125.7	H8'2—C8'—H8'3	109.5
C3—N2—H2	125.7	O5—C9—O6	123.0 (3)
C13—N3—C10	105.7 (3)	O5—C9—C10	118.2 (3)
C13—N3—Mg1	144.0 (2)	O6—C9—C10	118.8 (3)
C10—N3—Mg1	109.6 (2)	N3—C10—C11	110.4 (3)
C13—N4—C11	108.7 (3)	N3—C10—C9	117.6 (3)
C13—N4—H4	125.6	C11—C10—C9	131.9 (3)
C11—N4—H4	125.6	N4—C11—C10	105.0 (3)
C1—O1—Mg1	118.6 (2)	N4—C11—C12	122.6 (3)
C4—O3—H3	109.5	C10—C11—C12	132.3 (3)
C9—O5—Mg1	117.5 (2)	O8—C12—O7	123.4 (3)
C12—O7—H7	109.5	O8—C12—C11	120.1 (3)
Mg1—O9—H9C	119.2	O7—C12—C11	116.5 (3)
Mg1—O9—H9D	130.5	N3—C13—N4	110.1 (3)
H9C—O9—H9D	108.5	N3—C13—C14'	125.5 (9)
Mg1—O10—H10C	107.2	N4—C13—C14'	121.5 (9)
Mg1—O10—H10D	140.1	N3—C13—C14	125.3 (7)
H10C—O10—H10D	108.2	N4—C13—C14	124.0 (7)
H11C—O11—H11D	108.6	C13—C14—C15	110.3 (9)
H12C—O12—H12D	108.7	C13—C14—H14A	109.6
H13C—O13—H13D	107.8	C15—C14—H14A	109.6
H14G—O14—H14H	108.8	C13—C14—H14B	109.6
O1—C1—O2	125.2 (3)	C15—C14—H14B	109.6
O1—C1—C2	116.1 (3)	H14A—C14—H14B	108.1
O2—C1—C2	118.6 (3)	C16—C15—C14	113.1 (11)
N1—C2—C3	110.1 (3)	C16—C15—H15A	109.0
N1—C2—C1	118.1 (3)	C14—C15—H15A	109.0
C3—C2—C1	131.7 (3)	C16—C15—H15B	109.0
N2—C3—C2	104.8 (3)	C14—C15—H15B	109.0
N2—C3—C4	121.6 (3)	H15A—C15—H15B	107.8
C2—C3—C4	133.5 (3)	C13—C14'—C15'	113.6 (16)
O4—C4—O3	121.5 (3)	C13—C14'—H14C	108.9
O4—C4—C3	121.4 (3)	C15'—C14'—H14C	108.9
O3—C4—C3	117.1 (3)	C13—C14'—H14D	108.9
N1—C5—N2	110.3 (3)	C15'—C14'—H14D	108.9
N1—C5—C6	124.3 (5)	H14C—C14'—H14D	107.7
N2—C5—C6	125.0 (5)	C16'—C15'—C14'	111 (2)
N1—C5—C6'	126.9 (12)	C16'—C15'—H15C	109.3
N2—C5—C6'	118.1 (12)	C14'—C15'—H15C	109.3
C5—C6—C7	110.8 (7)	C16'—C15'—H15D	109.3
C5—C6—H6A	109.5	C14'—C15'—H15D	109.3
C7—C6—H6A	109.5	H15C—C15'—H15D	108.0
C5—C6—H6B	109.5	C15'—C16'—H16D	109.5
C7—C6—H6B	109.5	C15'—C16'—H16E	109.5
H6A—C6—H6B	108.1	H16D—C16'—H16E	109.5
C6—C7—C8	109.9 (6)	C15'—C16'—H16F	109.5
C6—C7—H7A	109.7	H16D—C16'—H16F	109.5
C8—C7—H7A	109.7	H16E—C16'—H16F	109.5
C6—C7—H7B	109.7

O10—Mg1—N1—C5	79.7 (4)	C2—N1—C5—C6'	−156.2 (14)
O1—Mg1—N1—C5	174.6 (4)	Mg1—N1—C5—C6'	26.8 (15)
O5—Mg1—N1—C5	−15.4 (4)	C3—N2—C5—N1	1.0 (4)
N3—Mg1—N1—C5	−92.2 (4)	C3—N2—C5—C6	−172.1 (6)
O10—Mg1—N1—C2	−97.2 (2)	C3—N2—C5—C6'	158.3 (13)
O1—Mg1—N1—C2	−2.28 (19)	N1—C5—C6—C7	97.0 (7)
O5—Mg1—N1—C2	167.7 (2)	N2—C5—C6—C7	−90.8 (8)
N3—Mg1—N1—C2	90.9 (2)	C6'—C5—C6—C7	−8 (3)
O9—Mg1—N3—C13	81.6 (4)	C5—C6—C7—C8	−173.2 (6)
O1—Mg1—N3—C13	−11.7 (4)	N1—C5—C6'—C7'	−100.8 (18)
O5—Mg1—N3—C13	174.1 (4)	N2—C5—C6'—C7'	106.1 (17)
N1—Mg1—N3—C13	−89.1 (4)	C6—C5—C6'—C7'	−6.8 (19)
O9—Mg1—N3—C10	−87.2 (2)	C5—C6'—C7'—C8'	−70 (2)
O1—Mg1—N3—C10	179.55 (19)	Mg1—O5—C9—O6	−174.7 (2)
O5—Mg1—N3—C10	5.30 (19)	Mg1—O5—C9—C10	5.3 (4)
N1—Mg1—N3—C10	102.1 (2)	C13—N3—C10—C11	−0.2 (3)
O9—Mg1—O1—C1	−179.6 (2)	Mg1—N3—C10—C11	173.0 (2)
O10—Mg1—O1—C1	88.9 (2)	C13—N3—C10—C9	−177.8 (3)
O5—Mg1—O1—C1	−59.6 (6)	Mg1—N3—C10—C9	−4.6 (3)
N1—Mg1—O1—C1	2.5 (2)	O5—C9—C10—N3	−0.1 (4)
N3—Mg1—O1—C1	−89.5 (2)	O6—C9—C10—N3	180.0 (3)
O9—Mg1—O5—C9	83.4 (2)	O5—C9—C10—C11	−177.1 (3)
O10—Mg1—O5—C9	174.8 (2)	O6—C9—C10—C11	2.9 (5)
O1—Mg1—O5—C9	−36.7 (6)	C13—N4—C11—C10	−0.3 (3)
N1—Mg1—O5—C9	−97.1 (2)	C13—N4—C11—C12	178.3 (3)
N3—Mg1—O5—C9	−5.9 (2)	N3—C10—C11—N4	0.3 (3)
Mg1—O1—C1—O2	177.7 (3)	C9—C10—C11—N4	177.5 (3)
Mg1—O1—C1—C2	−2.2 (4)	N3—C10—C11—C12	−178.1 (3)
C5—N1—C2—C3	1.2 (4)	C9—C10—C11—C12	−0.9 (6)
Mg1—N1—C2—C3	179.3 (2)	N4—C11—C12—O8	0.3 (5)
C5—N1—C2—C1	−176.1 (3)	C10—C11—C12—O8	178.4 (3)
Mg1—N1—C2—C1	2.0 (3)	N4—C11—C12—O7	−179.3 (3)
O1—C1—C2—N1	0.0 (4)	C10—C11—C12—O7	−1.1 (5)
O2—C1—C2—N1	180.0 (3)	C10—N3—C13—N4	0.0 (4)
O1—C1—C2—C3	−176.7 (3)	Mg1—N3—C13—N4	−169.0 (3)
O2—C1—C2—C3	3.4 (5)	C10—N3—C13—C14'	−161.0 (8)
C5—N2—C3—C2	−0.2 (4)	Mg1—N3—C13—C14'	29.9 (9)
C5—N2—C3—C4	177.5 (3)	C10—N3—C13—C14	171.5 (7)
N1—C2—C3—N2	−0.6 (3)	Mg1—N3—C13—C14	2.5 (8)
C1—C2—C3—N2	176.2 (3)	C11—N4—C13—N3	0.2 (4)
N1—C2—C3—C4	−178.0 (3)	C11—N4—C13—C14'	162.1 (8)
C1—C2—C3—C4	−1.1 (6)	C11—N4—C13—C14	−171.5 (7)
N2—C3—C4—O4	0.9 (5)	N3—C13—C14—C15	122.3 (10)
C2—C3—C4—O4	177.9 (3)	N4—C13—C14—C15	−67.3 (11)
N2—C3—C4—O3	−178.4 (3)	C14'—C13—C14—C15	24 (3)
C2—C3—C4—O3	−1.4 (6)	C13—C14—C15—C16	−63.5 (15)
C2—N1—C5—N2	−1.4 (4)	N3—C13—C14'—C15'	81.0 (19)
Mg1—N1—C5—N2	−178.4 (3)	N4—C13—C14'—C15'	−78.0 (18)
C2—N1—C5—C6	171.8 (6)	C14—C13—C14'—C15'	179 (5)
Mg1—N1—C5—C6	−5.2 (8)	C13—C14'—C15'—C16'	−173.1 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O8^iv	0.85	2.06	2.905 (3)	174
O11—H11C···O2^v	0.85	1.95	2.794 (3)	172
O11—H11D···O5^vi	0.85	2.05	2.893 (3)	172
O12—H12C···O7^vi	0.85	2.05	2.888 (4)	167
O12—H12D···O14^v	0.85	1.84	2.672 (6)	167
O13—H13C···O14	0.85	1.85	2.643 (6)	156
O13—H13D···O11^vii	0.85	2.07	2.869 (5)	156
O14—H14G···O1^viii	0.85	2.00	2.816 (5)	162
O14—H14H···O1^ix	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.

Experimental details

Crystal data
Chemical formula	[Mg(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O
M_r	517.74
Crystal system, space group	Triclinic, 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)
V (Å³)	1239.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.48 × 0.38 × 0.35

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.935, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	6478, 4321, 2780
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.178, 1.00
No. of reflections	4321
No. of parameters	378
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···O8^iv	0.85	2.06	2.905 (3)	174
O11—H11C···O2^v	0.85	1.95	2.794 (3)	172
O11—H11D···O5^vi	0.85	2.05	2.893 (3)	172
O12—H12C···O7^vi	0.85	2.05	2.888 (4)	167
O12—H12D···O14^v	0.85	1.84	2.672 (6)	167
O13—H13C···O14	0.85	1.85	2.643 (6)	156
O13—H13D···O11^vii	0.85	2.07	2.869 (5)	156
O14—H14G···O1^viii	0.85	2.00	2.816 (5)	162
O14—H14H···O1^ix	0.85	1.98	2.799 (5)	162

Acknowledgements

The authors thank Henan University of Urban Construction.

References

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