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

In the title compound, [MnCl(2)(C(11)H(13)N(5))], 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 dihydro-imidazole rings adopt envelope conformations. In the crystal structure, mol-ecules 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 = 341.10

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.187

S = 0.95

3317 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.53 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014354/ci2778sup1.cif

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

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

[MnCl2(C11H13N5)]	F(000) = 692
Mr = 341.10	Dx = 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

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

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(Fo2) + (0.0956P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
3317 reflections	Δρmax = 0.68 e Å−3
173 parameters	Δρmin = −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)

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	1.09096 (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*

	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)

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

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

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) ; (ii) .