[2,6-Bis(4,5-dihydro-1H-imidazol-2-yl)pyridine]dichloridomanganese(II)

Ren, C.-X.; Li, S.-Y.; Yin, Z.-Z.; Lu, X.; Ding, Y.-Q.

doi:10.1107/S1600536809014354

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m572-m573

doi:10.1107/S1600536809014354

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[2,6-Bis(4,5-dihydro-1H-imidazol-2-yl)pyridine]dichloridomanganese(II)

Chun-Xia Ren,^a ^* Su-Yun Li,^b Zhao-Zhong Yin,^a Xiang Lu ^a and Yu-Qiang Ding ^a

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China, and ^bDepartment of Public Education, Jiangxi Vocational and Technical College of Electricity, 8 Mailu Road, Nanchang, Jiangxi Province 330032, People's Republic of China
^*Correspondence e-mail: chunxiaren@sina.com

(Received 10 April 2009; accepted 17 April 2009; online 25 April 2009)

In the title compound, [MnCl₂(C₁₁H₁₃N₅)], the Mn^II ion is five-coordinated in a distorted square-pyramidal geometry, with three N atoms from the neutral tridentate 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine ligand and one chloride ion forming the basal plane and the other chloride ion in the apical position. Both dihydroimidazole rings adopt envelope conformations. In the crystal structure, molecules are linked into a three-dimensional network by N—H⋯Cl and C—H⋯Cl hydrogen bonds.

Related literature

For the synthesis of 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine, see: Baker et al. (1991 ). For general background, see: Bordo et al. (2001 ); Hagrman et al. (1999 ); Yaghi et al. (1998 ). For related structures, see: Böca et al. (2005 ); Haga et al. (1996 ); Hammes et al. (2005 ); Ren, Ye, He et al. (2004 ); Ren, Ye, Zhu et al. (2004 ); Ren et al. (2007 ); Stupka et al. (2004 ); Sun et al. (2008 ).

Experimental

Crystal data

[MnCl₂(C₁₁H₁₃N₅)]
M_r = 341.10
Monoclinic, P 2₁ /n
a = 9.297 (5) Å
b = 12.686 (7) Å
c = 12.383 (6) Å
β = 100.313 (9)°
V = 1436.9 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 273 K
0.30 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 1998 ) T_min = 0.700, T_max = 0.774
8507 measured reflections
3317 independent reflections
1750 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.187
S = 0.95
3317 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N2	2.234 (4)
Mn1—N4	2.237 (4)
Mn1—N3	2.244 (4)
Mn1—Cl1	2.3759 (19)
Mn1—Cl2	2.3842 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯Cl2ⁱ	0.86	2.46	3.287 (5)	161
N1—H1⋯Cl1ⁱⁱ	0.86	2.50	3.261 (5)	147
C7—H7⋯Cl2ⁱ	0.93	2.78	3.681 (6)	164
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536809014354/ci2778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014354/ci2778Isup2.hkl

checkCIF report

Comment top

The construction supramolecular architectures is currently of great interest owing to their intriguing network topologies and potential functions such as adsorption, ion exchange, shape-selective catalysis, non-linear and magnetic materials (Yaghi et al., 1998; Hagrman et al., 1999). The protonation and deprotonation of an imidazole ligand is believed to play an important role in the mechanism of the coordination chemistry (Bordo et al., 2001). We described previously a number of such metal complexes with imidazole ligands, and concluded that hydrogen bonding involving this group influences the geometry around the metal atom and the crystallization mechanism (Ren, Ye, He et al., 2004; Ren, Ye, Zhu et al., 2004; Ren et al., 2007; Sun et al., 2008). We report here the crystal structure of the title mononuclear coordination complex, [Mn(bip)Cl₂], where bip is 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine.

As shown in Fig. 1, in the title compound the manganese(II) atom is five-coordinated in a distorted square-pyramidal geometry, with three N atoms from the neutral tridentate bip ligand and one Cl^- ion (Cl1) forming the basal plane and the other Cl^- ion (Cl2) in the apical position. The Mn1 atom deviates from the Cl1-N2-N3-N4 plane by 0.5633 (7) Å towards the Cl2 atom. The Mn—N bond lengths of 2.234 (4), 2.237 (4), 2.244 (4) Å are slightly shorter than those observed in metal-imidazole systems (Stupka et al., 2004; Hammes et al., 2005; Haga et al., 1996; Böca et al., 2005). The N—Mn—N bond angles lie in the range 70.69 (14)–140.86 (14)°.

Adjacent molecules are linked into a three-dimensional network by N—H···Cl and C—H···Cl hydrogen bonds (Table 1).

Related literature top

For the synthesis of 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine, see: Baker et al. (1991). For general background, see: Bordo et al. (2001); Hagrman et al. (1999); Yaghi et al. (1998). For related structures, see: Böca et al. (2005); Haga et al. (1996); Hammes et al. (2005); Ren, Ye, He et al. (2004); Ren, Ye, Zhu et al. (2004); Ren et al. (2007); Stupka et al. (2004); Sun et al. (2008).

Experimental top

All the reagents and solvents employed were commercially available and used as received without further purification. The ligand 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine (bip) was synthesized by literature methods (Baker et al., 1991). A solution of MnCl₂.4H₂O (0.2 mmol, 40 mg) in acetonitrile (10 ml) was added dropwise to a stirred solution of bip (0.4 mmol, 86 mg) in methanol (10 ml) at 333 K. Yellow single crystals suitable for X-ray diffraction were obtained by slow diffusion of diethyl ether into the clear filtrate for 2 d in 60% yield. Main IR bands (KBr, cm_-1): 3365m, 3251 s, 1621w, 1596m, 1573 s, 1523m, 1446 s, 1275 s, 1026m, 957w, 822w, 745w, 663w.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 molecular structure of the [Mn(bip)Cl₂] complex, showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of [Mn(bip)Cl₂] viewed along the a axis. H atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds.

[2,6-Bis(4,5-dihydro-1H-imidazol-2-yl)pyridine]dichloridomanganese(II) top

Crystal data top

[MnCl₂(C₁₁H₁₃N₅)]	F(000) = 692
M_r = 341.10	D_x = 1.577 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1365 reflections
a = 9.297 (5) Å	θ = 2.3–23.1°
b = 12.686 (7) Å	µ = 1.28 mm⁻¹
c = 12.383 (6) Å	T = 273 K
β = 100.313 (9)°	Block, yellow
V = 1436.9 (13) Å³	0.30 × 0.25 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3317 independent reflections
Radiation source: fine-focus sealed tube	1750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS, Bruker, 1998)	h = −10→12
T_min = 0.700, T_max = 0.774	k = −10→16
8507 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.187	w = 1/[σ²(F_o²) + (0.0956P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.001
3317 reflections	Δρ_max = 0.68 e Å⁻³
173 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

Crystal data top

[MnCl₂(C₁₁H₁₃N₅)]	V = 1436.9 (13) Å³
M_r = 341.10	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.297 (5) Å	µ = 1.28 mm⁻¹
b = 12.686 (7) Å	T = 273 K
c = 12.383 (6) Å	0.30 × 0.25 × 0.21 mm
β = 100.313 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3317 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 1998)	1750 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.774	R_int = 0.077
8507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 0.95	Δρ_max = 0.68 e Å⁻³
3317 reflections	Δρ_min = −0.53 e Å⁻³
173 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	1.09096 (8)	0.66191 (6)	0.31687 (6)	0.0431 (3)
Cl1	1.33924 (15)	0.63750 (13)	0.29973 (12)	0.0605 (5)
Cl2	0.96929 (17)	0.77218 (13)	0.17311 (13)	0.0697 (5)
N1	0.9960 (5)	0.8515 (3)	0.5846 (4)	0.0519 (12)
H1	0.9262	0.8644	0.6198	0.062*
N2	1.1031 (5)	0.7757 (3)	0.4559 (3)	0.0492 (11)
N3	0.9235 (4)	0.6172 (3)	0.4186 (3)	0.0360 (9)
N4	0.9927 (4)	0.5062 (3)	0.2597 (3)	0.0458 (11)
N5	0.8274 (5)	0.3790 (4)	0.2646 (4)	0.0542 (12)
H5A	0.7647	0.3429	0.2923	0.065*
C1	1.1869 (7)	0.8745 (5)	0.4878 (5)	0.0587 (16)
H1A	1.1677	0.9266	0.4297	0.070*
H1B	1.2911	0.8606	0.5045	0.070*
C2	1.1298 (6)	0.9119 (5)	0.5908 (5)	0.0606 (16)
H2A	1.1988	0.8957	0.6573	0.073*
H2B	1.1103	0.9870	0.5881	0.073*
C3	1.0010 (5)	0.7721 (4)	0.5141 (4)	0.0413 (12)
C4	0.8964 (5)	0.6824 (4)	0.4970 (4)	0.0359 (11)
C5	0.7820 (5)	0.6653 (4)	0.5540 (4)	0.0432 (12)
H5	0.7626	0.7126	0.6069	0.052*
C6	0.6986 (6)	0.5756 (4)	0.5292 (4)	0.0510 (14)
H6	0.6222	0.5613	0.5662	0.061*
C7	0.7285 (5)	0.5069 (4)	0.4493 (4)	0.0474 (13)
H7	0.6737	0.4459	0.4325	0.057*
C8	0.8416 (5)	0.5311 (4)	0.3951 (4)	0.0387 (11)
C9	0.8875 (5)	0.4711 (4)	0.3049 (4)	0.0388 (11)
C10	0.8854 (7)	0.3506 (5)	0.1671 (5)	0.0618 (17)
H10A	0.8137	0.3615	0.1008	0.074*
H10B	0.9186	0.2781	0.1700	0.074*
C11	1.0136 (6)	0.4282 (5)	0.1743 (5)	0.0595 (16)
H11A	1.1062	0.3918	0.1950	0.071*
H11B	1.0123	0.4629	0.1043	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0457 (5)	0.0447 (5)	0.0447 (5)	−0.0006 (4)	0.0233 (4)	0.0035 (4)
Cl1	0.0490 (8)	0.0707 (10)	0.0689 (9)	0.0051 (7)	0.0298 (7)	0.0207 (8)
Cl2	0.0638 (10)	0.0713 (11)	0.0796 (11)	0.0170 (8)	0.0280 (8)	0.0339 (9)
N1	0.056 (3)	0.046 (3)	0.061 (3)	−0.016 (2)	0.029 (2)	−0.013 (2)
N2	0.050 (3)	0.049 (3)	0.054 (3)	−0.013 (2)	0.025 (2)	0.000 (2)
N3	0.041 (2)	0.034 (2)	0.035 (2)	−0.0027 (18)	0.0134 (18)	0.0013 (19)
N4	0.052 (3)	0.044 (3)	0.046 (2)	0.003 (2)	0.024 (2)	−0.002 (2)
N5	0.065 (3)	0.045 (3)	0.058 (3)	−0.009 (2)	0.025 (2)	−0.010 (2)
C1	0.062 (4)	0.048 (3)	0.071 (4)	−0.015 (3)	0.027 (3)	−0.001 (3)
C2	0.065 (4)	0.054 (4)	0.066 (4)	−0.014 (3)	0.021 (3)	−0.011 (3)
C3	0.042 (3)	0.044 (3)	0.040 (3)	−0.003 (2)	0.014 (2)	0.002 (2)
C4	0.043 (3)	0.032 (3)	0.036 (2)	−0.001 (2)	0.017 (2)	0.004 (2)
C5	0.049 (3)	0.045 (3)	0.041 (3)	−0.002 (3)	0.021 (2)	0.001 (2)
C6	0.054 (3)	0.050 (3)	0.058 (3)	−0.004 (3)	0.034 (3)	0.004 (3)
C7	0.043 (3)	0.048 (3)	0.055 (3)	−0.008 (3)	0.020 (3)	0.000 (3)
C8	0.039 (3)	0.037 (3)	0.042 (3)	0.003 (2)	0.013 (2)	0.004 (2)
C9	0.046 (3)	0.032 (3)	0.039 (3)	0.003 (2)	0.009 (2)	0.004 (2)
C10	0.076 (4)	0.056 (4)	0.056 (3)	0.012 (3)	0.017 (3)	−0.012 (3)
C11	0.066 (4)	0.064 (4)	0.054 (3)	0.003 (3)	0.027 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Mn1—N2	2.234 (4)	C1—H1A	0.97
Mn1—N4	2.237 (4)	C1—H1B	0.97
Mn1—N3	2.244 (4)	C2—H2A	0.97
Mn1—Cl1	2.3759 (19)	C2—H2B	0.97
Mn1—Cl2	2.3842 (18)	C3—C4	1.486 (7)
N1—C3	1.340 (7)	C4—C5	1.397 (6)
N1—C2	1.450 (7)	C5—C6	1.380 (8)
N1—H1	0.86	C5—H5	0.93
N2—C3	1.291 (6)	C6—C7	1.382 (7)
N2—C1	1.489 (7)	C6—H6	0.93
N3—C4	1.333 (6)	C7—C8	1.380 (6)
N3—C8	1.333 (6)	C7—H7	0.93
N4—C9	1.289 (6)	C8—C9	1.476 (7)
N4—C11	1.487 (7)	C10—C11	1.535 (9)
N5—C9	1.352 (7)	C10—H10A	0.97
N5—C10	1.455 (7)	C10—H10B	0.97
N5—H5A	0.86	C11—H11A	0.97
C1—C2	1.542 (8)	C11—H11B	0.97

N2—Mn1—N4	140.86 (14)	C1—C2—H2B	111.3
N2—Mn1—N3	71.04 (14)	H2A—C2—H2B	109.2
N4—Mn1—N3	70.69 (14)	N2—C3—N1	116.8 (5)
N2—Mn1—Cl1	103.72 (12)	N2—C3—C4	118.3 (5)
N4—Mn1—Cl1	101.82 (11)	N1—C3—C4	124.8 (4)
N3—Mn1—Cl1	143.13 (12)	N3—C4—C5	122.1 (5)
N2—Mn1—Cl2	98.52 (13)	N3—C4—C3	112.1 (4)
N4—Mn1—Cl2	99.76 (12)	C5—C4—C3	125.8 (4)
N3—Mn1—Cl2	106.47 (12)	C6—C5—C4	117.7 (5)
Cl1—Mn1—Cl2	110.39 (6)	C6—C5—H5	121.2
C3—N1—C2	107.6 (4)	C4—C5—H5	121.2
C3—N1—H1	126.2	C5—C6—C7	120.1 (5)
C2—N1—H1	126.2	C5—C6—H6	119.9
C3—N2—C1	106.5 (4)	C7—C6—H6	119.9
C3—N2—Mn1	117.8 (4)	C8—C7—C6	118.6 (5)
C1—N2—Mn1	134.3 (3)	C8—C7—H7	120.7
C4—N3—C8	119.6 (4)	C6—C7—H7	120.7
C4—N3—Mn1	119.4 (3)	N3—C8—C7	121.9 (5)
C8—N3—Mn1	120.7 (3)	N3—C8—C9	110.9 (4)
C9—N4—C11	106.5 (5)	C7—C8—C9	127.1 (5)
C9—N4—Mn1	117.8 (3)	N4—C9—N5	115.8 (5)
C11—N4—Mn1	135.6 (3)	N4—C9—C8	119.6 (5)
C9—N5—C10	109.2 (5)	N5—C9—C8	124.5 (4)
C9—N5—H5A	125.4	N5—C10—C11	101.1 (5)
C10—N5—H5A	125.4	N5—C10—H10A	111.6
N2—C1—C2	103.7 (4)	C11—C10—H10A	111.6
N2—C1—H1A	111.0	N5—C10—H10B	111.6
C2—C1—H1A	111.0	C11—C10—H10B	111.6
N2—C1—H1B	111.0	H10A—C10—H10B	109.4
C2—C1—H1B	111.0	N4—C11—C10	105.6 (4)
H1A—C1—H1B	109.0	N4—C11—H11A	110.6
N1—C2—C1	102.3 (5)	C10—C11—H11A	110.6
N1—C2—H2A	111.3	N4—C11—H11B	110.6
C1—C2—H2A	111.3	C10—C11—H11B	110.6
N1—C2—H2B	111.3	H11A—C11—H11B	108.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···Cl2ⁱ	0.86	2.46	3.287 (5)	161
N1—H1···Cl1ⁱⁱ	0.86	2.50	3.261 (5)	147
C7—H7···Cl2ⁱ	0.93	2.78	3.681 (6)	164

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

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₁H₁₃N₅)]
M_r	341.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	9.297 (5), 12.686 (7), 12.383 (6)
β (°)	100.313 (9)
V (Å³)	1436.9 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.30 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS, Bruker, 1998)
T_min, T_max	0.700, 0.774
No. of measured, independent and observed [I > 2σ(I)] reflections	8507, 3317, 1750
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.187, 0.95
No. of reflections	3317
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.53

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—N2	2.234 (4)	Mn1—Cl1	2.3759 (19)
Mn1—N4	2.237 (4)	Mn1—Cl2	2.3842 (18)
Mn1—N3	2.244 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···Cl2ⁱ	0.86	2.46	3.287 (5)	161
N1—H1···Cl1ⁱⁱ	0.86	2.50	3.261 (5)	147
C7—H7···Cl2ⁱ	0.93	2.78	3.681 (6)	164

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

Acknowledgements

This work was generously supported by the National Natural Science Foundation of China (grant No. 20701016).

References

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