Diaqua­bis­(4-carb­oxy-2-ethyl-1H-imidazole-5-carboxyl­ato-κ2N3,O4)manganese(II) N,N-dimethyl­formamide disolvate

Zhang, G.; Wang, Y.

doi:10.1107/S1600536811020071

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m828

doi:10.1107/S1600536811020071

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Diaquabis(4-carboxy-2-ethyl-1H-imidazole-5-carboxylato-κ²N³,O⁴)manganese(II) N,N-dimethylformamide disolvate

Gang Zhang ^a ^* and Yong Wang ^b

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan, People's Republic of China, and ^bDepartment of Chemical Engineering, Henan Polytechnic Institute, Nanyang, 473009, People's Republic of China
^*Correspondence e-mail: zhanghn1010@163.com

(Received 18 May 2011; accepted 26 May 2011; online 4 June 2011)

In the title compound, [Mn(C₇H₇N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the central Mn^II ion, located on an inversion center, is hexacoordinated by four O atoms from two water molecules and two carboxylate groups, and two N atoms from two 4-carboxy-2-ethyl-1H-imidazole-5-carboxylate anions in a slightly distorted octahedral environment. The complex molecules and solvent molecules are connected via N—H⋯O and O—H⋯O hydrogen bonds into a two-dimensional polymeric structure parallel to (001).

Related literature

For coordination polymers built from 2-ethyl-4,5-imidazoledicarboxylic acid, see: Li et al. (2011 ); Wang et al. (2008 ); Zhang et al. (2010 ). For the structure of the analogous Mn^II complex with a 5-carboxy-2-ethyl-1H-imidazole-4-carboxylate ligand, see: Yan et al. (2010 ).

Experimental

Crystal data

[Mn(C₇H₇N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r = 603.46
Triclinic, $[P \overline 1]$
a = 7.3246 (2) Å
b = 9.0070 (2) Å
c = 12.0541 (3) Å
α = 68.841 (1)°
β = 77.780 (1)°
γ = 70.132 (1)°
V = 693.89 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.899, T_max = 0.908
5239 measured reflections
2447 independent reflections
2192 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.04
2447 reflections
182 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O1ⁱ	0.80	1.92	2.707 (2)	165
O1W—H1W⋯O2ⁱⁱ	0.82	1.96	2.768 (2)	168
N2—H2⋯O5	0.86	1.89	2.740 (2)	168
O3—H3⋯O2	0.82	1.64	2.462 (2)	179
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z.

Data collection: APEX2 (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); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020071/gk2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020071/gk2378Isup2.hkl

checkCIF report

Comment top

Self-assembly of supramolecular architectures based on imidazole carboxylate ligands has drawn much attention during recent decades. To the best of our knowledge, coordination polymers based on 2-ethyl-4,5-imidazoledicarboxylate ligand has been reperted only in recent years (Wang et al., 2008; Zhang et al., 2010; Li et al., 2011). Herein we report the title compound obtained by the reaction of manganese chloride with 2-ethyl-4,5-imidazoledicarboxylic acid (H₃EIDC) in a N,N-dimethylformamide solution under hydrothermal conditions.

The title compound, [Mn(C₇H₇N₂O₄)₂(H₂O)₂].2C₃H₇NO, depicted in Fig. 1. Each Mn^II is coordinated by two terminal water molecules, two nitrogen atoms and two oxygen atoms from two chelating 2-ethyl-4,5-imidazoledicarboxylate ligands, generating a distorted octahedral coordination environment. The N,N-dimethylformamide molecules are connected to the complex molecule via hydrogen bond between N2 and O6 atoms (Table 1). In each H₂EIDC ligand that chelates Mn^II ion via its N, O atom there is a strong hydrogen bond between the carboxylic and carboxylate groups.

A two-dimensional suramolecular structure is consolidated by intermolecular hydrogen-bonding interactions (N—H···O and O—H···O).

The structure of the title compound is very similar to that formed by 2-propyl-4,5-imidazoledicarboxylate ligand with Mn(II) (Yan et al., 2010).

Related literature top

For coordination polymers built with 2-ethyl-4,5-imidazoledicarboxylic acid, see: Li et al. (2011); Wang et al. (2008); Zhang et al. (2010). For the structure of the analogous Mn^II complex with a 5-carboxy-2-ethyl-1H-imidazole-4-carboxylate ligand, see: Yan et al. (2010).

Experimental top

A mixture of MnCl₂ (0.5 mmol, 0.06 g) and 2-ethyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.95 g) in 15 ml of DMF solution was placed in a 23 ml Teflon-lined reactor, which was heated to 443 K for 4 days, and then cooled to room temperature at a rate of 5 K h^-1. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids [symmetry codes: (i) 2 - x, -y, -z.]

Diaquabis(4-carboxy-2-ethyl-1H-imidazole-5-carboxylato- κ²N³,O⁴)manganese(II) N,N-dimethylformamide disolvate top

Crystal data top

[Mn(C₇H₇N₂O₄)₂(H₂O)₂]·2C₃H₇NO	Z = 1
M_r = 603.46	F(000) = 315
Triclinic, P1	D_x = 1.444 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3246 (2) Å	Cell parameters from 5837 reflections
b = 9.0070 (2) Å	θ = 2.8–27.9°
c = 12.0541 (3) Å	µ = 0.54 mm⁻¹
α = 68.841 (1)°	T = 296 K
β = 77.780 (1)°	Block, colorless
γ = 70.132 (1)°	0.20 × 0.20 × 0.18 mm
V = 693.89 (3) Å³

Data collection top

Bruker APEXII area-detector diffractometer	2447 independent reflections
Radiation source: fine-focus sealed tube	2192 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.899, T_max = 0.908	k = −10→10
5239 measured reflections	l = −13→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0528P)² + 0.2406P] where P = (F_o² + 2F_c²)/3
2447 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.33 e Å⁻³
3 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Mn(C₇H₇N₂O₄)₂(H₂O)₂]·2C₃H₇NO	γ = 70.132 (1)°
M_r = 603.46	V = 693.89 (3) Å³
Triclinic, P1	Z = 1
a = 7.3246 (2) Å	Mo Kα radiation
b = 9.0070 (2) Å	µ = 0.54 mm⁻¹
c = 12.0541 (3) Å	T = 296 K
α = 68.841 (1)°	0.20 × 0.20 × 0.18 mm
β = 77.780 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2447 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2192 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.908	R_int = 0.017
5239 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
2447 reflections	Δρ_min = −0.21 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq
Mn1	1.0000	0.0000	0.0000	0.03597 (17)
O1	0.5096 (2)	0.68752 (18)	0.13763 (14)	0.0455 (4)
O2	0.6923 (2)	0.70548 (17)	−0.03711 (13)	0.0431 (4)
O3	0.8948 (3)	0.52116 (18)	−0.15377 (14)	0.0483 (4)
H3	0.8284	0.5834	−0.1154	0.072*
O4	1.0038 (2)	−0.25098 (18)	0.12795 (13)	0.0420 (4)
O5	0.3937 (3)	0.3980 (3)	0.39973 (17)	0.0701 (6)
N1	0.8058 (2)	0.17558 (19)	0.09645 (15)	0.0341 (4)
N2	0.6175 (3)	0.3399 (2)	0.19823 (15)	0.0362 (4)
H2	0.5413	0.3718	0.2554	0.043*
N3	0.2062 (3)	0.5787 (3)	0.49596 (18)	0.0519 (5)
C1	0.6958 (3)	0.1811 (3)	0.19781 (18)	0.0387 (5)
C2	0.6797 (3)	0.4415 (2)	0.09255 (17)	0.0298 (4)
C3	0.7965 (3)	0.3374 (2)	0.02988 (17)	0.0292 (4)
C4	0.6210 (3)	0.6249 (2)	0.06428 (18)	0.0337 (4)
C5	0.9031 (3)	0.3697 (2)	−0.09070 (17)	0.0330 (4)
C6	0.6624 (4)	0.0344 (3)	0.2986 (2)	0.0594 (7)
H6A	0.7410	−0.0656	0.2792	0.071*
H6B	0.7080	0.0322	0.3693	0.071*
C7	0.4567 (6)	0.0304 (5)	0.3278 (4)	0.1004 (13)
H7A	0.3757	0.1320	0.3423	0.151*
H7B	0.4466	−0.0620	0.3980	0.151*
H7C	0.4145	0.0187	0.2620	0.151*
C8	0.2127 (5)	0.4520 (5)	0.6120 (2)	0.0766 (9)
H8A	0.2852	0.3454	0.6029	0.115*
H8B	0.0822	0.4508	0.6464	0.115*
H8C	0.2748	0.4761	0.6634	0.115*
C9	0.1012 (6)	0.7462 (5)	0.4934 (4)	0.1007 (13)
H9A	0.0953	0.8174	0.4120	0.151*
H9B	0.1668	0.7829	0.5350	0.151*
H9C	−0.0288	0.7505	0.5315	0.151*
C10	0.2976 (4)	0.5403 (4)	0.3999 (2)	0.0603 (7)
H10	0.2897	0.6254	0.3272	0.072*
O1W	0.7541 (2)	0.0082 (2)	−0.07777 (18)	0.0579 (5)
H1W	0.7407	−0.0852	−0.0560	0.087*
H2W	0.6611	0.0895	−0.0898	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0376 (3)	0.0226 (2)	0.0446 (3)	−0.00243 (18)	0.00243 (19)	−0.01653 (19)
O1	0.0533 (9)	0.0297 (8)	0.0465 (9)	0.0017 (7)	0.0006 (7)	−0.0197 (7)
O2	0.0565 (9)	0.0226 (7)	0.0465 (9)	−0.0090 (7)	0.0017 (7)	−0.0127 (7)
O3	0.0653 (11)	0.0272 (8)	0.0415 (8)	−0.0125 (7)	0.0157 (7)	−0.0109 (7)
O4	0.0489 (9)	0.0306 (8)	0.0404 (8)	−0.0073 (7)	0.0118 (7)	−0.0173 (6)
O5	0.0795 (13)	0.0729 (14)	0.0570 (11)	−0.0180 (11)	0.0185 (10)	−0.0372 (10)
N1	0.0374 (9)	0.0228 (8)	0.0362 (9)	−0.0041 (7)	0.0038 (7)	−0.0110 (7)
N2	0.0416 (9)	0.0293 (9)	0.0313 (9)	−0.0032 (7)	0.0044 (7)	−0.0131 (7)
N3	0.0464 (11)	0.0616 (13)	0.0494 (12)	−0.0141 (10)	0.0077 (9)	−0.0278 (10)
C1	0.0434 (12)	0.0274 (11)	0.0364 (11)	−0.0047 (9)	0.0022 (9)	−0.0086 (9)
C2	0.0311 (10)	0.0254 (10)	0.0317 (10)	−0.0042 (8)	−0.0032 (8)	−0.0112 (8)
C3	0.0304 (9)	0.0224 (9)	0.0331 (10)	−0.0047 (7)	−0.0007 (8)	−0.0108 (8)
C4	0.0360 (10)	0.0267 (10)	0.0382 (11)	−0.0031 (8)	−0.0064 (9)	−0.0141 (9)
C5	0.0358 (10)	0.0265 (10)	0.0346 (10)	−0.0080 (8)	0.0020 (8)	−0.0114 (8)
C6	0.0736 (18)	0.0351 (13)	0.0485 (14)	−0.0099 (12)	0.0116 (12)	−0.0043 (11)
C7	0.109 (3)	0.093 (3)	0.088 (2)	−0.064 (2)	−0.007 (2)	0.014 (2)
C8	0.091 (2)	0.096 (2)	0.0454 (15)	−0.0368 (19)	0.0138 (15)	−0.0275 (16)
C9	0.085 (2)	0.084 (3)	0.129 (3)	−0.006 (2)	0.011 (2)	−0.058 (3)
C10	0.0607 (16)	0.072 (2)	0.0449 (14)	−0.0210 (14)	0.0073 (12)	−0.0204 (13)
O1W	0.0502 (9)	0.0266 (8)	0.0991 (14)	−0.0010 (7)	−0.0228 (9)	−0.0230 (9)

Geometric parameters (Å, º) top

Mn1—O1Wⁱ	2.1683 (17)	C1—C6	1.489 (3)
Mn1—O1W	2.1683 (17)	C2—C3	1.369 (3)
Mn1—O4ⁱ	2.2244 (15)	C2—C4	1.484 (3)
Mn1—O4	2.2244 (15)	C3—C5	1.475 (3)
Mn1—N1ⁱ	2.2302 (15)	C5—O4ⁱ	1.238 (2)
Mn1—N1	2.2302 (15)	C6—C7	1.483 (5)
O1—C4	1.228 (2)	C6—H6A	0.9700
O2—C4	1.281 (3)	C6—H6B	0.9700
O3—C5	1.287 (2)	C7—H7A	0.9600
O3—H3	0.8200	C7—H7B	0.9600
O4—C5ⁱ	1.238 (2)	C7—H7C	0.9600
O5—C10	1.235 (4)	C8—H8A	0.9600
N1—C1	1.321 (3)	C8—H8B	0.9600
N1—C3	1.373 (2)	C8—H8C	0.9600
N2—C1	1.350 (3)	C9—H9A	0.9600
N2—C2	1.365 (3)	C9—H9B	0.9600
N2—H2	0.8600	C9—H9C	0.9600
N3—C10	1.309 (3)	C10—H10	0.9300
N3—C9	1.434 (4)	O1W—H1W	0.8200
N3—C8	1.449 (4)	O1W—H2W	0.8047

O1Wⁱ—Mn1—O1W	180.00 (10)	O1—C4—C2	118.76 (18)
O1Wⁱ—Mn1—O4ⁱ	90.79 (6)	O2—C4—C2	116.00 (17)
O1W—Mn1—O4ⁱ	89.21 (6)	O4ⁱ—C5—O3	122.34 (18)
O1Wⁱ—Mn1—O4	89.21 (6)	O4ⁱ—C5—C3	119.06 (18)
O1W—Mn1—O4	90.79 (6)	O3—C5—C3	118.59 (17)
O4ⁱ—Mn1—O4	180.00 (11)	C7—C6—C1	115.0 (2)
O1Wⁱ—Mn1—N1ⁱ	90.95 (6)	C7—C6—H6A	108.5
O1W—Mn1—N1ⁱ	89.05 (6)	C1—C6—H6A	108.5
O4ⁱ—Mn1—N1ⁱ	104.47 (5)	C7—C6—H6B	108.5
O4—Mn1—N1ⁱ	75.53 (5)	C1—C6—H6B	108.5
O1Wⁱ—Mn1—N1	89.05 (6)	H6A—C6—H6B	107.5
O1W—Mn1—N1	90.95 (6)	C6—C7—H7A	109.5
O4ⁱ—Mn1—N1	75.53 (5)	C6—C7—H7B	109.5
O4—Mn1—N1	104.47 (5)	H7A—C7—H7B	109.5
N1ⁱ—Mn1—N1	180.00 (7)	C6—C7—H7C	109.5
C5—O3—H3	109.5	H7A—C7—H7C	109.5
C5ⁱ—O4—Mn1	115.88 (12)	H7B—C7—H7C	109.5
C1—N1—C3	106.19 (16)	N3—C8—H8A	109.5
C1—N1—Mn1	142.61 (14)	N3—C8—H8B	109.5
C3—N1—Mn1	111.18 (12)	H8A—C8—H8B	109.5
C1—N2—C2	108.45 (17)	N3—C8—H8C	109.5
C1—N2—H2	125.8	H8A—C8—H8C	109.5
C2—N2—H2	125.8	H8B—C8—H8C	109.5
C10—N3—C9	122.6 (3)	N3—C9—H9A	109.5
C10—N3—C8	120.8 (3)	N3—C9—H9B	109.5
C9—N3—C8	116.6 (3)	H9A—C9—H9B	109.5
N1—C1—N2	110.34 (18)	N3—C9—H9C	109.5
N1—C1—C6	125.5 (2)	H9A—C9—H9C	109.5
N2—C1—C6	124.14 (19)	H9B—C9—H9C	109.5
N2—C2—C3	105.31 (17)	O5—C10—N3	124.1 (3)
N2—C2—C4	122.29 (17)	O5—C10—H10	118.0
C3—C2—C4	132.40 (18)	N3—C10—H10	118.0
C2—C3—N1	109.70 (16)	Mn1—O1W—H1W	109.5
C2—C3—C5	132.07 (18)	Mn1—O1W—H2W	120.7
N1—C3—C5	118.21 (16)	H1W—O1W—H2W	120.8
O1—C4—O2	125.24 (19)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ⁱⁱ	0.80	1.92	2.707 (2)	165
O1W—H1W···O2ⁱⁱⁱ	0.82	1.96	2.768 (2)	168
N2—H2···O5	0.86	1.89	2.740 (2)	168
O3—H3···O2	0.82	1.64	2.462 (2)	179

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

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₇N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r	603.46
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3246 (2), 9.0070 (2), 12.0541 (3)
α, β, γ (°)	68.841 (1), 77.780 (1), 70.132 (1)
V (Å³)	693.89 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.899, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	5239, 2447, 2192
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.04
No. of reflections	2447
No. of parameters	182
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ⁱ	0.80	1.92	2.707 (2)	165
O1W—H1W···O2ⁱⁱ	0.82	1.96	2.768 (2)	168
N2—H2···O5	0.86	1.89	2.740 (2)	168
O3—H3···O2	0.82	1.64	2.462 (2)	179

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

Acknowledgements

The authors acknowledge Henan University of Urban Construction for supporting this work.

References

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