Diaqua-bis-(4-carb-oxy-2-ethyl-1H-imidazole-5-carboxyl-ato-κN,O)manganese(II) N,N-dimethyl-formamide disolvate.

In the title compound, [Mn(C(7)H(7)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the central Mn(II) ion, located on an inversion center, is hexa-coordinated by four O atoms from two water mol-ecules and two carboxyl-ate groups, and two N atoms from two 4-carb-oxy-2-ethyl-1H-imidazole-5-carboxyl-ate anions in a slightly distorted octa-hedral environment. The complex mol-ecules and solvent mol-ecules 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 MnII 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 = 603.46

Triclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.04

2447 reflections

182 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020071/gk2378sup1.cif

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

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

[Mn(C7H7N2O4)2(H2O)2]·2C3H7NO	Z = 1
Mr = 603.46	F(000) = 315
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0528P)2 + 0.2406P] where P = (Fo2 + 2Fc2)/3
2447 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.33 e Å−3
3 restraints	Δρmin = −0.21 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
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*

	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)

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)

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

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) ; (ii) .