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

Yan, J.-B.; Li, S.-J.; Song, W.-D.; Wang, H.; Miao, D.-L.

doi:10.1107/S1600536809054634

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m99

doi:10.1107/S1600536809054634

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

Jian-Bin Yan,^a Shi-Jie Li,^a Wen-Dong Song,^a ^* Hao Wang ^a and Dong-Liang Miao ^a

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 14 December 2009; accepted 18 December 2009; online 24 December 2009)

In the title complex, [Mn(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the Mn^II atom, lying on an inversion centre, is six-coordinated by two N,O-bidentate 5-carboxy-2-propyl-1H-imidazole-4-carboxylate ligands and two water molecules in a distorted octahedral environment. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a two-dimensional supramolecular 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_r = 631.51
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.05
2508 reflections
191 parameters
27 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+1, -y, -z+1; (ii) -x, -y+1, -z; (iii) x-1, 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: SHELXTL.

Supporting information

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

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

checkCIF report

Comment top

Structures of complexes containing metals and N-heterocyclic carboxylic acids have attracted much attention. The N-heterocyclic carboxylic acids can function as multidentate ligands, exhibiting diverse structrual types, and their metal complexes can be potentially used as functional materials (Liang et al., 2002; Net et al., 1989; Nie et al., 2007). Recently, we have reported a new complex, poly[diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato- κ³N³,O⁴:O⁵)calcium(II)] (Song et al., 2010). In this paper, we report the synthesis and structure of a Mn^II complex obtained under hydrothermal conditions.

As illustrated in Fig. 1, the title complex molecule contains one Mn^II atom, lying on an inversion centre, one mono-deprotonated 5-carboxy-2-propyl-1H-imidazole-4-carboxylate ligand, one coordinated water molecule and one dimethylformamide solvent molecule in the asymmetric unit. The Mn^II atom is six-coordinated by two N,O-bidentate ligands and two water molecules in a distorted octahedral environment (Table 1). In the crystal structure, a two-dimensional supramolecular network is formed by N—H···O and O—H···O hydrogen bonds (Table 2 and Fig. 2).

Related literature top

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 top

A mixture of MnCl₂ (0.5 mmol, 0.06 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of dimethylformamide solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 433 K for 4 d. 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 30% probability level. [Symmetry code: (i) -x, 2 - y, -z.]
	Fig. 2. A view of the two-dimensional network constructed by O—H···O and N—H···O hydrogen bonds (dashed lines).

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

Crystal data top

[Mn(C₈H₉N₂O₄)₂H₂O)₂]·2C₃H₇NO	Z = 1
M_r = 631.51	F(000) = 331
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2131 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
ϕ and ω scan	θ_max = 25.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996))	h = −8→8
T_min = 0.847, T_max = 0.896	k = −9→11
3653 measured reflections	l = −13→12
2508 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0549P)² + 0.120P] where P = (F_o² + 2F_c²)/3
2508 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.34 e Å⁻³
27 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Mn(C₈H₉N₂O₄)₂H₂O)₂]·2C₃H₇NO	γ = 68.863 (1)°
M_r = 631.51	V = 708.89 (14) Å³
Triclinic, P1	Z = 1
a = 7.3992 (8) Å	Mo Kα radiation
b = 9.4429 (11) Å	µ = 0.54 mm⁻¹
c = 11.1978 (13) Å	T = 273 K
α = 76.591 (1)°	0.32 × 0.25 × 0.21 mm
β = 87.927 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2508 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996))	2131 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.896	R_int = 0.025
3653 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	27 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
2508 reflections	Δρ_min = −0.32 e Å⁻³
191 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.84	2.11	2.927 (2)	164

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

Experimental details

Crystal data
Chemical formula	[Mn(C₈H₉N₂O₄)₂H₂O)₂]·2C₃H₇NO
M_r	631.51
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.3992 (8), 9.4429 (11), 11.1978 (13)
α, β, γ (°)	76.591 (1), 87.927 (1), 68.863 (1)
V (Å³)	708.89 (14)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.32 × 0.25 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996))
T_min, T_max	0.847, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	3653, 2508, 2131
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.05
No. of reflections	2508
No. of parameters	191
No. of restraints	27
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32

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

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

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