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

In the title complex, [Mn(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Mn(II) atom, lying on an inversion centre, is six-coordinated by two N,O-bidentate 5-carb-oxy-2-propyl-1H-imidazole-4-carb-oxyl-ate ligands and two water mol-ecules in a distorted octa-hedral environment. In the crystal structure, the complex mol-ecules and dimethyl-formamide solvent mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into a two-dimensional supra-molecular network parallel to (001).

Related literature

For the potential uses and diverse structural types of complexes containing metals and N-heterocyclic carboxylic acids, see: Liang et al. (2002 ▶); Net et al. (1989 ▶); Nie et al. (2007 ▶); Song et al. (2010 ▶).

Experimental

Crystal data

[Mn(C8H9N2O4)2(H2O)2]·2C3H7NO

M = 631.51

Triclinic,

a = 7.3992 (8) Å

b = 9.4429 (11) Å

c = 11.1978 (13) Å

α = 76.591 (1)°

β = 87.927 (1)°

γ = 68.863 (1)°

V = 708.89 (14) Å3

Z = 1

Mo Kα radiation

μ = 0.54 mm−1

T = 273 K

0.32 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶)) T min = 0.847, T max = 0.896

3653 measured reflections

2508 independent reflections

2131 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.05

2508 reflections

191 parameters

27 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.32 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054634/hy2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054634/hy2265Isup2.hkl

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

[Mn(C8H9N2O4)2H2O)2]·2C3H7NO	Z = 1
Mr = 631.51	F(000) = 331
Triclinic, P1	Dx = 1.479 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3992 (8) Å	Cell parameters from 3600 reflections
b = 9.4429 (11) Å	θ = 1.4–28°
c = 11.1978 (13) Å	µ = 0.54 mm−1
α = 76.591 (1)°	T = 273 K
β = 87.927 (1)°	Block, colourless
γ = 68.863 (1)°	0.32 × 0.25 × 0.21 mm
V = 708.89 (14) Å3

Bruker APEXII CCD diffractometer	2131 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
φ and ω scan	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996))	h = −8→8
Tmin = 0.847, Tmax = 0.896	k = −9→11
3653 measured reflections	l = −13→12
2508 independent 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.120P] where P = (Fo2 + 2Fc2)/3
2508 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.34 e Å−3
27 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
Mn1	0.0000	1.0000	0.0000	0.03110 (18)
O1	−0.0548 (3)	0.92199 (19)	−0.16620 (15)	0.0379 (4)
O1W	−0.2795 (2)	0.9893 (2)	0.06711 (17)	0.0434 (4)
H1W	−0.2933	0.9113	0.0484	0.065*
H2W	−0.3672	1.0743	0.0329	0.065*
O2	0.0012 (3)	0.7160 (2)	−0.24509 (15)	0.0424 (4)
O3	0.1886 (3)	0.4324 (2)	−0.18355 (17)	0.0469 (5)
H3	0.1294	0.5271	−0.2021	0.070*
O4	0.3630 (3)	0.25664 (19)	−0.02155 (18)	0.0456 (5)
N1	0.1434 (3)	0.7447 (2)	0.04969 (16)	0.0279 (4)
N2	0.3073 (3)	0.4924 (2)	0.10599 (17)	0.0312 (4)
H2	0.3782	0.4030	0.1504	0.037*
C1	0.1335 (3)	0.6770 (2)	−0.0454 (2)	0.0261 (5)
C2	0.2340 (3)	0.5196 (3)	−0.0111 (2)	0.0285 (5)
C3	0.2498 (3)	0.6292 (3)	0.1400 (2)	0.0303 (5)
C4	0.0194 (3)	0.7798 (3)	−0.1592 (2)	0.0306 (5)
C5	0.2661 (3)	0.3927 (3)	−0.0755 (2)	0.0337 (5)
C6	0.2933 (4)	0.6449 (3)	0.2642 (2)	0.0410 (6)
H6A	0.2584	0.7548	0.2625	0.049*
H6B	0.4317	0.5939	0.2840	0.049*
C7	0.1855 (5)	0.5745 (4)	0.3637 (3)	0.0616 (8)
H7A	0.0477	0.6206	0.3409	0.074*
H7B	0.2268	0.4633	0.3688	0.074*
C8	0.2178 (5)	0.5986 (4)	0.4887 (3)	0.0648 (9)
H8A	0.3457	0.5307	0.5217	0.097*
H8B	0.1234	0.5753	0.5427	0.097*
H8C	0.2049	0.7052	0.4811	0.097*
O9	0.4607 (3)	−0.2429 (2)	0.7294 (2)	0.0626 (6)
N5	0.3789 (3)	0.0120 (3)	0.6354 (2)	0.0470 (6)
C17	0.4889 (4)	−0.1190 (4)	0.7092 (3)	0.0501 (7)
H17	0.5962	−0.1181	0.7492	0.060*
C18	0.2038 (5)	0.0185 (4)	0.5761 (3)	0.0702 (10)
H18A	0.0937	0.0641	0.6212	0.105*
H18B	0.2138	−0.0852	0.5745	0.105*
H18C	0.1880	0.0810	0.4936	0.105*
C19	0.4104 (7)	0.1561 (4)	0.6248 (4)	0.0879 (12)
H19A	0.5309	0.1353	0.6673	0.132*
H19B	0.3061	0.2259	0.6604	0.132*
H19C	0.4151	0.2033	0.5396	0.132*

	U11	U22	U33	U12	U13	U23
Mn1	0.0369 (3)	0.0180 (3)	0.0364 (3)	−0.0063 (2)	−0.0014 (2)	−0.0080 (2)
O1	0.0483 (10)	0.0222 (9)	0.0367 (9)	−0.0057 (8)	−0.0087 (7)	−0.0043 (7)
O1W	0.0411 (10)	0.0287 (9)	0.0616 (12)	−0.0120 (8)	0.0038 (8)	−0.0142 (8)
O2	0.0568 (11)	0.0346 (10)	0.0329 (9)	−0.0101 (9)	−0.0099 (8)	−0.0112 (8)
O3	0.0609 (12)	0.0307 (10)	0.0473 (11)	−0.0079 (9)	−0.0035 (9)	−0.0189 (8)
O4	0.0465 (10)	0.0218 (9)	0.0645 (12)	−0.0044 (8)	−0.0026 (9)	−0.0145 (8)
N1	0.0344 (10)	0.0210 (10)	0.0277 (10)	−0.0092 (8)	−0.0017 (8)	−0.0055 (8)
N2	0.0332 (10)	0.0188 (9)	0.0351 (11)	−0.0048 (8)	−0.0052 (8)	−0.0002 (8)
C1	0.0279 (11)	0.0210 (11)	0.0294 (11)	−0.0085 (9)	0.0007 (9)	−0.0064 (9)
C2	0.0288 (11)	0.0228 (12)	0.0341 (12)	−0.0087 (9)	0.0016 (9)	−0.0083 (9)
C3	0.0340 (12)	0.0234 (12)	0.0328 (12)	−0.0106 (10)	−0.0036 (9)	−0.0040 (9)
C4	0.0330 (12)	0.0272 (12)	0.0295 (12)	−0.0087 (10)	−0.0024 (9)	−0.0055 (10)
C5	0.0326 (12)	0.0267 (13)	0.0440 (14)	−0.0105 (10)	0.0066 (10)	−0.0138 (11)
C6	0.0512 (15)	0.0365 (14)	0.0354 (13)	−0.0164 (12)	−0.0098 (11)	−0.0062 (11)
C7	0.072 (2)	0.076 (2)	0.0455 (16)	−0.0325 (18)	0.0089 (15)	−0.0238 (15)
C8	0.069 (2)	0.077 (2)	0.0424 (16)	−0.0168 (19)	0.0026 (15)	−0.0191 (16)
O9	0.0712 (14)	0.0298 (11)	0.0699 (14)	−0.0062 (10)	−0.0216 (11)	0.0047 (10)
N5	0.0535 (13)	0.0309 (12)	0.0502 (13)	−0.0098 (11)	0.0019 (11)	−0.0065 (10)
C17	0.0472 (15)	0.0471 (18)	0.0500 (16)	−0.0084 (14)	−0.0051 (13)	−0.0129 (13)
C18	0.0575 (19)	0.058 (2)	0.073 (2)	−0.0073 (16)	−0.0120 (16)	0.0061 (17)
C19	0.134 (4)	0.050 (2)	0.089 (3)	−0.044 (2)	0.019 (3)	−0.0182 (19)

Mn1—N1	2.1960 (18)	C6—H6A	0.9700
Mn1—O1W	2.2036 (17)	C6—H6B	0.9700
Mn1—O1	2.2530 (17)	C7—C8	1.509 (4)
O1—C4	1.238 (3)	C7—H7A	0.9700
O1W—H1W	0.8509	C7—H7B	0.9700
O1W—H2W	0.8436	C8—H8A	0.9600
O2—C4	1.282 (3)	C8—H8B	0.9600
O3—C5	1.272 (3)	C8—H8C	0.9600
O3—H3	0.8200	O9—C17	1.229 (4)
O4—C5	1.240 (3)	N5—C17	1.313 (4)
N1—C3	1.326 (3)	N5—C19	1.440 (4)
N1—C1	1.379 (3)	N5—C18	1.452 (4)
N2—C3	1.347 (3)	C17—H17	0.9300
N2—C2	1.369 (3)	C18—H18A	0.9600
N2—H2	0.8600	C18—H18B	0.9600
C1—C2	1.367 (3)	C18—H18C	0.9600
C1—C4	1.480 (3)	C19—H19A	0.9600
C2—C5	1.481 (3)	C19—H19B	0.9600
C3—C6	1.491 (3)	C19—H19C	0.9600
C6—C7	1.516 (4)
N1i—Mn1—N1	180.0	O4—C5—C2	118.9 (2)
N1i—Mn1—O1W	87.40 (7)	O3—C5—C2	116.6 (2)
N1—Mn1—O1W	92.60 (6)	C3—C6—C7	112.7 (2)
N1i—Mn1—O1Wi	92.60 (6)	C3—C6—H6A	109.1
N1—Mn1—O1Wi	87.40 (7)	C7—C6—H6A	109.1
O1W—Mn1—O1Wi	180.0	C3—C6—H6B	109.1
N1i—Mn1—O1i	75.41 (6)	C7—C6—H6B	109.1
N1—Mn1—O1i	104.59 (6)	H6A—C6—H6B	107.8
O1W—Mn1—O1i	91.40 (6)	C8—C7—C6	113.4 (3)
O1Wi—Mn1—O1i	88.60 (6)	C8—C7—H7A	108.9
N1i—Mn1—O1	104.59 (6)	C6—C7—H7A	108.9
N1—Mn1—O1	75.41 (6)	C8—C7—H7B	108.9
O1W—Mn1—O1	88.60 (6)	C6—C7—H7B	108.9
O1Wi—Mn1—O1	91.40 (6)	H7A—C7—H7B	107.7
O1i—Mn1—O1	180.0	C7—C8—H8A	109.5
C4—O1—Mn1	115.45 (14)	C7—C8—H8B	109.5
Mn1—O1W—H1W	107.7	H8A—C8—H8B	109.5
Mn1—O1W—H2W	107.5	C7—C8—H8C	109.5
H1W—O1W—H2W	112.0	H8A—C8—H8C	109.5
C5—O3—H3	109.5	H8B—C8—H8C	109.5
C3—N1—C1	105.96 (18)	C17—N5—C19	121.9 (3)
C3—N1—Mn1	141.35 (15)	C17—N5—C18	119.5 (3)
C1—N1—Mn1	112.53 (13)	C19—N5—C18	118.0 (3)
C3—N2—C2	108.51 (18)	O9—C17—N5	125.0 (3)
C3—N2—H2	125.7	O9—C17—H17	117.5
C2—N2—H2	125.7	N5—C17—H17	117.5
C2—C1—N1	109.72 (19)	N5—C18—H18A	109.5
C2—C1—C4	132.5 (2)	N5—C18—H18B	109.5
N1—C1—C4	117.81 (19)	H18A—C18—H18B	109.5
C1—C2—N2	105.37 (19)	N5—C18—H18C	109.5
C1—C2—C5	132.1 (2)	H18A—C18—H18C	109.5
N2—C2—C5	122.5 (2)	H18B—C18—H18C	109.5
N1—C3—N2	110.44 (19)	N5—C19—H19A	109.5
N1—C3—C6	125.5 (2)	N5—C19—H19B	109.5
N2—C3—C6	124.0 (2)	H19A—C19—H19B	109.5
O1—C4—O2	123.4 (2)	N5—C19—H19C	109.5
O1—C4—C1	118.6 (2)	H19A—C19—H19C	109.5
O2—C4—C1	117.9 (2)	H19B—C19—H19C	109.5
O4—C5—O3	124.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O9ii	0.86	1.84	2.682 (3)	165
O3—H3···O2	0.82	1.65	2.471 (2)	176
O1W—H1W···O4iii	0.85	1.92	2.764 (2)	170
O1W—H2W···O4iv	0.84	2.11	2.927 (2)	164

Table 1

Selected bond lengths (Å)

Mn1—N1	2.1960 (18)
Mn1—O1W	2.2036 (17)
Mn1—O1	2.2530 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O9i	0.86	1.84	2.682 (3)	165
O3—H3⋯O2	0.82	1.65	2.471 (2)	176
O1W—H1W⋯O4ii	0.85	1.92	2.764 (2)	170
O1W—H2W⋯O4iii	0.84	2.11	2.927 (2)	164

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