Diaqua­[5,5′-dicarb­oxy-2,2′-(propane-1,3-di­yl)bis­(1H-imidazole-4-carboxyl­ato)]manganese(II)

Yang, H.-X.; Zhou, X.; Jin, G.; Meng, X.-R.

doi:10.1107/S1600536811012566

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m560

doi:10.1107/S1600536811012566

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Diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato)]manganese(II)

Huai-Xia Yang,^a ^* Xiaoli Zhou,^b Guanghua Jin ^c and Xiang-Ru Meng ^c

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, ^bExperiment Administrative Center, Zhongzhou University, Zhengzhou 450044, People's Republic of China, and ^cDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: yanghuaixia888@163.com

(Received 30 March 2011; accepted 4 April 2011; online 7 April 2011)

The complex molecule of the title compound, [Mn(C₁₃H₁₀N₄O₈)(H₂O)₂] or [Mn(H₄pbidc)(H₂O)₂] (H₆pbidc = 2,2′-(propane-1,3-diyl)bis(1H-imidazole-4,5-dicarboxylic acid), has 2 symmetry with the twofold rotation axis running through the Mn²⁺ cation and the central C atom of the propanediyl unit. The cation is six-coordinated by two N atoms and two O atoms from one H₄pbidc²⁻ anion and two water O atoms in a considerably distorted octahedral coordination. In the crystal, adjacent molecules are linked through O—H⋯O and N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background to complexes based on 1H-imidazole-4,5-dicarboxylic acid, see: Ghosh et al. (2009 ); Liu et al. (2008 ); Sun & Yang (2007 ).

Experimental

Crystal data

[Mn(C₁₃H₁₀N₄O₈)(H₂O)₂]
M_r = 441.22
Monoclinic, C 2/c
a = 15.620 (3) Å
b = 8.5310 (17) Å
c = 12.739 (3) Å
β = 97.07 (3)°
V = 1684.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.828, T_max = 0.862
3426 measured reflections
1464 independent reflections
1265 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.090
S = 1.09
1464 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O5	2.107 (2)
Mn1—N1	2.237 (2)
Mn1—O1	2.3236 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H2W⋯O4ⁱ	0.85	1.94	2.780 (3)	168
O5—H1W⋯O3ⁱⁱ	0.85	1.93	2.780 (3)	174
N2—H2A⋯O4ⁱⁱⁱ	0.86	1.97	2.785 (3)	159
O3—H3⋯O2	0.85	1.68	2.527 (3)	178
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012566/wm2475sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012566/wm2475Isup2.hkl

checkCIF report

Comment top

Up to date, a large number of metal-organic frameworks derived from 1H-imidazole-4,5-dicarboxylic acid (H₃idc) have been synthesized since it is a good linker and can be successively deprotonated to generate H₂idc^-, Hidc^2- and idc^3- anions (Ghosh et al., 2009; Liu et al., 2008; Sun & Yang, 2007). Compared with H₃idc, 2,2'-(1,3-propanediyl)bis-1H-imidazole-4,5-dicarboxylic acid (H₆pbidc) can provide a greater tunability of structural frameworks because of the presence of the propanediyl spacer. However, complexes derived from this ligand have been scarcely reported. In this work, through the reaction of H₆pbidc with MnSO₄, we obtained the title complex [Mn(H₄pbidc) (H₂O)₂], (I).

As shown in Figure 1, the Mn²⁺ cation in (I) is hexacoordinated and features a distorted octahedral coordination geometry. N1, O1, N1A, O1A atoms from the tetradentate H₄pbidc^2- group coordinate to the cation in a chelating fashion and O5, O5A atoms from water molecules complete the coordination polyhedron. The entire complex molecule has symmetry 2. The bond angles around the Mn²⁺ cation significantly deviate from 90 or 180° (see supplementary material). Intramolecular O—H···O hydrogen bonds between the carboxyl/carboxylate groups stabilize the molecular configuration whereas O—H···O and N—H···O hydrogen bonds between the water molecules and carboxylate O atoms and between imidazole groups and carboxylate O atoms of adjacent molecules consolidate the crystal packing.

Related literature top

For background to complexes based on 1H-imidazole-4,5-dicarboxylic acid, see: Ghosh et al. (2009); Liu et al. (2008); Sun & Yang (2007).

Experimental top

A mixture of MnSO₄ (0.05 mmol), 2,2'-(1,3-propanediyl)bis-1H-imidazole-4,5-dicarboxylic (0.05 mmol), methanol (2 ml) and water (2 ml) was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 433 K for 72 h, then cooled to room temperature. Light yellow crystals with good quality were obtained from the filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title complex, showing the labelling of the atoms which are displayed with their displacement ellipsoids at the 30% probability level. [Symmetry code A: -x, y, -z + 1/2.]

Diaqua[5,5'-dicarboxy-2,2'-(propane-1,3-diyl)bis(1H-imidazole-4- carboxylato)]manganese(II) top

Crystal data top

[Mn(C₁₃H₁₀N₄O₈)(H₂O)₂]	F(000) = 900
M_r = 441.22	D_x = 1.740 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2738 reflections
a = 15.620 (3) Å	θ = 2.6–27.9°
b = 8.5310 (17) Å	µ = 0.85 mm⁻¹
c = 12.739 (3) Å	T = 293 K
β = 97.07 (3)°	Prism, light yellow
V = 1684.7 (6) Å³	0.23 × 0.21 × 0.18 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	1464 independent reflections
Radiation source: fine-focus sealed tube	1265 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ω scans	h = −17→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −10→8
T_min = 0.828, T_max = 0.862	l = −15→12
3426 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0405P)² + 1.7694P] where P = (F_o² + 2F_c²)/3
1464 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Mn(C₁₃H₁₀N₄O₈)(H₂O)₂]	V = 1684.7 (6) Å³
M_r = 441.22	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.620 (3) Å	µ = 0.85 mm⁻¹
b = 8.5310 (17) Å	T = 293 K
c = 12.739 (3) Å	0.23 × 0.21 × 0.18 mm
β = 97.07 (3)°

Data collection top

Rigaku Saturn diffractometer	1464 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	1265 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.862	R_int = 0.026
3426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.09	Δρ_max = 0.47 e Å⁻³
1464 reflections	Δρ_min = −0.45 e Å⁻³
128 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	0.0000	0.22580 (7)	0.2500	0.0249 (2)
N1	0.08997 (14)	0.4109 (3)	0.32272 (18)	0.0273 (5)
N2	0.16454 (14)	0.5985 (3)	0.40995 (19)	0.0308 (6)
H2A	0.1767	0.6876	0.4397	0.037*
O1	0.13833 (12)	0.1209 (2)	0.26815 (16)	0.0336 (5)
O2	0.27378 (12)	0.1518 (2)	0.34234 (17)	0.0382 (5)
O3	0.35729 (12)	0.3642 (2)	0.44866 (16)	0.0336 (5)
H3	0.3281	0.2937	0.4133	0.040*
O4	0.34141 (12)	0.6152 (2)	0.48617 (17)	0.0370 (5)
O5	0.00284 (13)	0.1299 (3)	0.09807 (16)	0.0466 (6)
H1W	−0.0390	0.1314	0.0487	0.056*
H2W	0.0460	0.1216	0.0637	0.056*
C1	0.19523 (18)	0.2024 (3)	0.3170 (2)	0.0278 (6)
C2	0.17401 (16)	0.3615 (3)	0.3491 (2)	0.0242 (6)
C3	0.22101 (16)	0.4777 (3)	0.4038 (2)	0.0258 (6)
C4	0.31248 (17)	0.4881 (3)	0.4495 (2)	0.0269 (6)
C5	0.08645 (17)	0.5546 (3)	0.3616 (2)	0.0297 (7)
C6	0.00932 (19)	0.6586 (4)	0.3507 (3)	0.0462 (9)
H6A	0.0130	0.7285	0.4111	0.055*
H6B	−0.0420	0.5947	0.3516	0.055*
C7	0.0000	0.7559 (5)	0.2500	0.0562 (15)
H7A	−0.0509	0.8214	0.2480	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0183 (3)	0.0268 (3)	0.0276 (3)	0.000	−0.0048 (2)	0.000
N1	0.0177 (11)	0.0278 (12)	0.0344 (13)	0.0007 (9)	−0.0048 (10)	−0.0048 (10)
N2	0.0222 (12)	0.0279 (12)	0.0396 (14)	−0.0003 (10)	−0.0068 (11)	−0.0085 (10)
O1	0.0237 (11)	0.0333 (11)	0.0416 (12)	0.0003 (9)	−0.0051 (9)	−0.0114 (9)
O2	0.0227 (11)	0.0373 (12)	0.0515 (13)	0.0084 (9)	−0.0078 (10)	−0.0074 (10)
O3	0.0208 (10)	0.0361 (12)	0.0408 (11)	−0.0011 (9)	−0.0094 (9)	−0.0059 (9)
O4	0.0236 (10)	0.0357 (12)	0.0490 (13)	−0.0055 (9)	−0.0062 (10)	−0.0099 (10)
O5	0.0241 (11)	0.0804 (17)	0.0328 (12)	0.0111 (11)	−0.0070 (10)	−0.0179 (11)
C1	0.0238 (15)	0.0319 (15)	0.0268 (14)	0.0015 (12)	−0.0008 (12)	−0.0008 (12)
C2	0.0174 (13)	0.0281 (14)	0.0262 (14)	0.0001 (11)	−0.0008 (12)	0.0002 (11)
C3	0.0191 (14)	0.0291 (14)	0.0278 (14)	−0.0010 (11)	−0.0028 (11)	−0.0012 (12)
C4	0.0206 (14)	0.0331 (16)	0.0261 (14)	−0.0018 (12)	−0.0002 (12)	0.0023 (12)
C5	0.0189 (14)	0.0298 (15)	0.0381 (16)	0.0004 (12)	−0.0054 (13)	−0.0094 (13)
C6	0.0235 (16)	0.0419 (18)	0.069 (2)	0.0065 (14)	−0.0091 (16)	−0.0271 (17)
C7	0.029 (2)	0.023 (2)	0.109 (5)	0.000	−0.020 (3)	0.000

Geometric parameters (Å, º) top

Mn1—O5	2.107 (2)	O3—H3	0.8500
Mn1—O5ⁱ	2.107 (2)	O4—C4	1.243 (3)
Mn1—N1	2.237 (2)	O5—H1W	0.8501
Mn1—N1ⁱ	2.237 (2)	O5—H2W	0.8500
Mn1—O1	2.3236 (19)	C1—C2	1.467 (4)
Mn1—O1ⁱ	2.3236 (19)	C2—C3	1.371 (4)
N1—C5	1.326 (3)	C3—C4	1.478 (4)
N1—C2	1.380 (3)	C5—C6	1.489 (4)
N2—C5	1.350 (3)	C6—C7	1.520 (4)
N2—C3	1.365 (3)	C6—H6A	0.9700
N2—H2A	0.8600	C6—H6B	0.9700
O1—C1	1.235 (3)	C7—C6ⁱ	1.520 (4)
O2—C1	1.303 (3)	C7—H7A	0.9700
O3—C4	1.269 (3)

O5—Mn1—O5ⁱ	134.29 (13)	H1W—O5—H2W	101.9
O5—Mn1—N1	124.84 (9)	O1—C1—O2	122.4 (3)
O5ⁱ—Mn1—N1	88.68 (8)	O1—C1—C2	119.2 (2)
O5—Mn1—N1ⁱ	88.68 (8)	O2—C1—C2	118.4 (2)
O5ⁱ—Mn1—N1ⁱ	124.84 (9)	C3—C2—N1	109.7 (2)
N1—Mn1—N1ⁱ	90.22 (11)	C3—C2—C1	133.2 (2)
O5—Mn1—O1	79.48 (8)	N1—C2—C1	117.1 (2)
O5ⁱ—Mn1—O1	83.31 (8)	N2—C3—C2	105.4 (2)
N1—Mn1—O1	72.64 (7)	N2—C3—C4	122.2 (2)
N1ⁱ—Mn1—O1	147.34 (8)	C2—C3—C4	132.4 (2)
O5—Mn1—O1ⁱ	83.31 (8)	O4—C4—O3	123.7 (2)
O5ⁱ—Mn1—O1ⁱ	79.48 (8)	O4—C4—C3	119.3 (2)
N1—Mn1—O1ⁱ	147.34 (8)	O3—C4—C3	117.0 (2)
N1ⁱ—Mn1—O1ⁱ	72.64 (7)	N1—C5—N2	110.5 (2)
O1—Mn1—O1ⁱ	134.71 (10)	N1—C5—C6	125.9 (2)
C5—N1—C2	105.8 (2)	N2—C5—C6	123.5 (2)
C5—N1—Mn1	138.97 (18)	C5—C6—C7	113.4 (3)
C2—N1—Mn1	114.56 (17)	C5—C6—H6A	108.9
C5—N2—C3	108.6 (2)	C7—C6—H6A	108.9
C5—N2—H2A	125.7	C5—C6—H6B	108.9
C3—N2—H2A	125.7	C7—C6—H6B	108.9
C1—O1—Mn1	115.86 (17)	H6A—C6—H6B	107.7
C4—O3—H3	109.4	C6ⁱ—C7—C6	113.7 (3)
Mn1—O5—H1W	124.9	C6ⁱ—C7—H7A	107.4
Mn1—O5—H2W	127.8	C6—C7—H7A	109.3

O5—Mn1—N1—C5	121.0 (3)	O2—C1—C2—C3	−0.1 (5)
O5ⁱ—Mn1—N1—C5	−92.4 (3)	O1—C1—C2—N1	0.3 (4)
N1ⁱ—Mn1—N1—C5	32.5 (3)	O2—C1—C2—N1	−178.9 (2)
O1—Mn1—N1—C5	−175.8 (3)	C5—N2—C3—C2	0.6 (3)
O1ⁱ—Mn1—N1—C5	−24.3 (4)	C5—N2—C3—C4	−179.9 (2)
O5—Mn1—N1—C2	−69.7 (2)	N1—C2—C3—N2	−0.2 (3)
O5ⁱ—Mn1—N1—C2	76.92 (19)	C1—C2—C3—N2	−179.0 (3)
N1ⁱ—Mn1—N1—C2	−158.2 (2)	N1—C2—C3—C4	−179.5 (3)
O1—Mn1—N1—C2	−6.49 (17)	C1—C2—C3—C4	1.6 (5)
O1ⁱ—Mn1—N1—C2	144.92 (17)	N2—C3—C4—O4	−6.9 (4)
O5—Mn1—O1—C1	138.8 (2)	C2—C3—C4—O4	172.4 (3)
O5ⁱ—Mn1—O1—C1	−83.7 (2)	N2—C3—C4—O3	173.2 (3)
N1—Mn1—O1—C1	7.01 (19)	C2—C3—C4—O3	−7.5 (4)
N1ⁱ—Mn1—O1—C1	68.3 (3)	C2—N1—C5—N2	0.8 (3)
O1ⁱ—Mn1—O1—C1	−151.7 (2)	Mn1—N1—C5—N2	170.6 (2)
Mn1—O1—C1—O2	172.9 (2)	C2—N1—C5—C6	178.2 (3)
Mn1—O1—C1—C2	−6.3 (3)	Mn1—N1—C5—C6	−11.9 (5)
C5—N1—C2—C3	−0.4 (3)	C3—N2—C5—N1	−0.9 (3)
Mn1—N1—C2—C3	−173.07 (18)	C3—N2—C5—C6	−178.5 (3)
C5—N1—C2—C1	178.7 (2)	N1—C5—C6—C7	−87.0 (4)
Mn1—N1—C2—C1	6.0 (3)	N2—C5—C6—C7	90.1 (4)
O1—C1—C2—C3	179.1 (3)	C5—C6—C7—C6ⁱ	60.5 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2W···O4ⁱⁱ	0.85	1.94	2.780 (3)	168
O5—H1W···O3ⁱⁱⁱ	0.85	1.93	2.780 (3)	174
N2—H2A···O4^iv	0.86	1.97	2.785 (3)	159
O3—H3···O2	0.85	1.68	2.527 (3)	178

Symmetry codes: (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₃H₁₀N₄O₈)(H₂O)₂]
M_r	441.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	15.620 (3), 8.5310 (17), 12.739 (3)
β (°)	97.07 (3)
V (Å³)	1684.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.828, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	3426, 1464, 1265
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.090, 1.09
No. of reflections	1464
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.45

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—O5	2.107 (2)	Mn1—O1	2.3236 (19)
Mn1—N1	2.237 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2W···O4ⁱ	0.85	1.94	2.780 (3)	168
O5—H1W···O3ⁱⁱ	0.85	1.93	2.780 (3)	174
N2—H2A···O4ⁱⁱⁱ	0.86	1.97	2.785 (3)	159
O3—H3···O2	0.85	1.68	2.527 (3)	178

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, −y+3/2, −z+1.

Acknowledgements

The study was supported by the Science and Technology Department of Henan Province (082102330003).

References

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m560

doi:10.1107/S1600536811012566

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­aqua­[5,5′-dicarb­­oxy-2,2′-(propane-1,3-di­yl)bis­­(1H-imidazole-4-carboxyl­ato)]manganese(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato)]manganese(II)