Poly[bis­[μ-1,4-bis­(imidazol-1-ylmeth­yl)benzene]­dichloridomanganese(II)]

Mei, C.-Z.; Shan, W.-W.; Li, K.-H.

doi:10.1107/S1600536811029485

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1156

doi:10.1107/S1600536811029485

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Poly[bis[μ-1,4-bis(imidazol-1-ylmethyl)benzene]dichloridomanganese(II)]

Chong-Zhen Mei,^a Wen-Wen Shan ^a ^* and Kai-Hui Li ^a

^aNorth China University of Water Conservancy and Electric Power, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: hbsysww@163.com

(Received 27 June 2011; accepted 21 July 2011; online 30 July 2011)

In the crystal structure of the title compound, [MnCl₂(C₁₄H₁₄N₄)₂]_n, the Mn^II atom, lying on an inversion center, is coordinated by four N atoms from four 1,4-bis(imidazol-1-ylmethyl)benzene (bimb) ligands and two Cl⁻ anions in a distorted octahedral geometry. The bimb ligands bridge the Mn^II atoms, forming a two-dimensional polymeric complex, which is composed of a 52-membered [Mn₄(bimb)₄] ring with distances of 7.7812 (2) and 27.4731 (9) Å between opposite metal atoms. Weak C—H⋯π interactions are present in the crystal structure.

Related literature

For the background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ); Ockwig et al. (2005 ); Zang et al. (2006 ); Zhang et al. (2009 ). For related syntheses and structures of compounds with a bimb ligand, see: Hoskins et al. (1997 ).

Experimental

Crystal data

[MnCl₂(C₁₄H₁₄N₄)₂]
M_r = 602.42
Monoclinic, P 2₁ /c
a = 7.7812 (2) Å
b = 12.7910 (3) Å
c = 14.2575 (4) Å
β = 105.539 (3)°
V = 1367.17 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.865, T_max = 0.877
3921 measured reflections
2367 independent reflections
2102 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.093
S = 1.04
2367 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N1	2.2695 (13)
Mn1—N3	2.2665 (14)
Mn1—Cl1	2.5639 (4)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N3,N4,C8–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cgⁱ	0.97	2.65	3.522 (2)	150
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029485/xu5253sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029485/xu5253Isup2.hkl

checkCIF report

Comment top

The supramolecular coordination assemblies are of great interest not only for their variety of architectures but also for the potential applications as functional materials (Maspoch et al., 2007; Ockwig et al., 2005). Many nitrogen-containing ligands have been successfully employed in the construction of the coordination compounds due to they can satisfy and even mediate the coordination needs of the metal center and consequently generate more meaningful architectures, in which supramolecular contacts (hydrogen bonding, π-π stacking) frequently occur (Zang et al., 2006; Zhang et al. 2009). To further explore various factors that influence the formation of result structures in the assembly reactions, we undertake synthetic and structural studies on one novel Mn(II) coordination polymers based on the highly flexible bidentate ligand 1,4-bis(imidazol-1-ylmethyl)-benzene (1,4-bimb): [Mn(bimb)₂Cl₂]_n).

The metal-ligand connectivity pattern of complex is depicted in Figure 1. There are one kind of Mn(II) ion, one kind of Cl^- and two kinds of bimb ligands in the structure. Metal center displays a symmetrical Cl₂N₄ octahedral geometry, and the related bond distances and bond angles are all symmetrically equivalent. Four N atoms from different bimb ligands comprise the equatorial plane, while two Cl^- occupy the axial positions. Each bimb ligand acts as a µ₂-bridge in trans-conformation with the planes of the two imidazole rings parallel. As shown in Figure 2, two rows of Mn(II) cations are linked together through bimb ligands to form a meso-helix running along the a-axis. Adjacent meso-helixes are associated together by sharing metal ions to form a two-dimensional architecture, in which large 52-membered rings [Mn₄(bimb)₄] with the opposite Mn···Mn distances being 7.7812 (2) Å and 27.4731 (9) Å are detected. If the metal center is considered as a four-connected node, the individual two-dimensional network can be described as a (4,4)-net. Further investigation shows that C8—H8···Cl1ⁱ hydrogen bonding is contribute to the stability of the layer. Neighboring layers are arranged parallel with the coordinated Cl^- closed to H2 atoms of imidazole ring from adjacent layer, and interlayer C2—H2···Cl1ⁱⁱ hydrogen bonds can be detected which lead to the formation of the three-dimensional supromolecular structure, as shown in Figure 3. The hydrogen-bonding geometry is listed in Table 1.

Related literature top

For the background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2006); Zhang et al. (2009). For related syntheses and structures of compounds with a bimb ligand, see: Hoskins et al. (1997).

Experimental top

1,4-Bis(imidazol-1-ylmethyl)-benzene (bimb) was prepared according to the literature (Hoskins et al., 1997), all other starting materials were of analytical grade and obtained from commercial sources without further purification. The title compound was synthesized hydrothermally in a Teflon-lined stainless steel container by heating a mixture of 1,4-bis(imidazol-1-ylmethyl)-benzene (bimb) (0.0119 g, 0.05 mmol), MnCl₂.4H₂O (0.0099 g, 0.05 mmol) and NaOH (0.0040 g, 0.1 mmol) in 7 ml of distilled water at 120°C for 3 days, and then cooled to room temperature. Yellow block crystals were obtained in 68% yield based on manganese.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Metal coordination and atom labeling in title compound (thermal ellipsoids at 50% probability level). All hydrogen atoms are omitted for clarity.
	Fig. 2. A view of the layer structure in compound 1. Mn atoms are drawn as polyhedrons.

Poly[bis[µ-1,4-bis(imidazol-1-ylmethyl)benzene]dichloridomanganese(II)] top

Crystal data top

[MnCl₂(C₁₄H₁₄N₄)₂]	F(000) = 622
M_r = 602.42	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2678 reflections
a = 7.7812 (2) Å	θ = 3.0–25.1°
b = 12.7910 (3) Å	µ = 0.71 mm⁻¹
c = 14.2575 (4) Å	T = 296 K
β = 105.539 (3)°	Block, yellow
V = 1367.17 (6) Å³	0.21 × 0.20 × 0.19 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2367 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.865, T_max = 0.877	k = −7→15
3921 measured reflections	l = −16→10

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
2367 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[MnCl₂(C₁₄H₁₄N₄)₂]	V = 1367.17 (6) Å³
M_r = 602.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7812 (2) Å	µ = 0.71 mm⁻¹
b = 12.7910 (3) Å	T = 296 K
c = 14.2575 (4) Å	0.21 × 0.20 × 0.19 mm
β = 105.539 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2102 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.877	R_int = 0.015
3921 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
2367 reflections	Δρ_min = −0.25 e Å⁻³
178 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	0.0000	0.0000	0.02539 (15)
N1	−0.0491 (2)	−0.09844 (11)	0.12272 (9)	0.0311 (3)
N2	−0.1216 (2)	−0.12917 (11)	0.25951 (10)	0.0313 (4)
N3	0.21756 (19)	0.07932 (11)	0.11619 (9)	0.0305 (3)
N4	0.3569 (2)	0.14248 (11)	0.26047 (10)	0.0314 (4)
Cl1	−0.22693 (6)	0.13438 (3)	0.02653 (3)	0.03544 (16)
C1	0.0739 (2)	−0.16467 (14)	0.18007 (12)	0.0330 (4)
H1	0.1721	−0.1924	0.1632	0.040*
C2	0.0323 (3)	−0.18392 (14)	0.26455 (12)	0.0332 (4)
H2	0.0952	−0.2257	0.3157	0.040*
C3	−0.1654 (2)	−0.07860 (14)	0.17360 (11)	0.0314 (4)
H3	−0.2644	−0.0354	0.1526	0.038*
C4	−0.2131 (3)	−0.11906 (15)	0.33668 (13)	0.0408 (5)
H4A	−0.2361	−0.1881	0.3587	0.049*
H4B	−0.3269	−0.0846	0.3107	0.049*
C5	−0.1034 (2)	−0.05720 (14)	0.42203 (12)	0.0315 (4)
C6	−0.0835 (3)	0.04960 (15)	0.41478 (12)	0.0377 (4)
H6	−0.1397	0.0835	0.3570	0.045*
C7	0.0182 (3)	0.10667 (15)	0.49176 (12)	0.0382 (5)
H7	0.0296	0.1786	0.4858	0.046*
C8	0.3906 (3)	0.10316 (15)	0.11778 (13)	0.0379 (4)
H8	0.4403	0.0942	0.0658	0.046*
C9	0.4773 (3)	0.14128 (15)	0.20553 (13)	0.0407 (5)
H9	0.5958	0.1627	0.2252	0.049*
C10	0.2038 (2)	0.10424 (13)	0.20375 (12)	0.0307 (4)
H10	0.1002	0.0962	0.2237	0.037*
C11	0.3886 (3)	0.17165 (15)	0.36308 (12)	0.0385 (5)
H11A	0.2796	0.2005	0.3731	0.046*
H11B	0.4790	0.2259	0.3784	0.046*
C12	0.4485 (2)	0.08073 (13)	0.43225 (11)	0.0287 (4)
C13	0.5545 (3)	0.10091 (14)	0.52584 (12)	0.0344 (4)
H13	0.5921	0.1688	0.5437	0.041*
C14	0.3964 (3)	−0.02103 (14)	0.40819 (12)	0.0347 (4)
H14	0.3263	−0.0358	0.3458	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0305 (2)	0.0259 (2)	0.0201 (2)	0.00112 (14)	0.00755 (16)	0.00075 (13)
N1	0.0381 (8)	0.0307 (8)	0.0249 (7)	−0.0003 (7)	0.0091 (6)	0.0020 (6)
N2	0.0398 (9)	0.0327 (8)	0.0225 (7)	−0.0088 (7)	0.0107 (6)	−0.0040 (6)
N3	0.0309 (8)	0.0342 (8)	0.0262 (7)	0.0028 (6)	0.0072 (6)	0.0002 (6)
N4	0.0355 (9)	0.0307 (8)	0.0246 (7)	0.0000 (6)	0.0019 (6)	0.0038 (6)
Cl1	0.0383 (3)	0.0308 (3)	0.0415 (3)	0.00726 (19)	0.0182 (2)	−0.00047 (18)
C1	0.0372 (10)	0.0295 (9)	0.0317 (9)	0.0010 (8)	0.0083 (8)	−0.0001 (7)
C2	0.0402 (10)	0.0321 (9)	0.0249 (8)	−0.0034 (8)	0.0045 (7)	0.0022 (7)
C3	0.0382 (10)	0.0319 (9)	0.0248 (8)	−0.0013 (8)	0.0097 (7)	−0.0006 (7)
C4	0.0500 (12)	0.0496 (12)	0.0279 (9)	−0.0173 (9)	0.0196 (9)	−0.0101 (8)
C5	0.0376 (10)	0.0340 (9)	0.0257 (8)	−0.0051 (8)	0.0136 (8)	−0.0053 (7)
C6	0.0496 (12)	0.0369 (10)	0.0243 (8)	0.0018 (9)	0.0061 (8)	0.0065 (8)
C7	0.0590 (13)	0.0260 (9)	0.0327 (10)	−0.0029 (9)	0.0175 (9)	0.0003 (7)
C8	0.0360 (11)	0.0464 (11)	0.0329 (10)	0.0021 (9)	0.0119 (8)	0.0010 (8)
C9	0.0305 (10)	0.0439 (11)	0.0443 (11)	−0.0025 (9)	0.0043 (9)	0.0059 (9)
C10	0.0310 (9)	0.0322 (9)	0.0281 (9)	−0.0011 (8)	0.0064 (7)	0.0012 (7)
C11	0.0523 (12)	0.0309 (10)	0.0262 (9)	−0.0010 (9)	0.0000 (8)	−0.0019 (8)
C12	0.0309 (9)	0.0292 (9)	0.0239 (8)	−0.0021 (7)	0.0035 (7)	−0.0009 (7)
C13	0.0425 (10)	0.0264 (9)	0.0292 (9)	−0.0078 (8)	0.0011 (8)	−0.0032 (7)
C14	0.0403 (11)	0.0346 (10)	0.0218 (8)	−0.0039 (8)	−0.0044 (8)	−0.0024 (7)

Geometric parameters (Å, º) top

Mn1—N1ⁱ	2.2695 (13)	C4—H4A	0.9700
Mn1—N1	2.2695 (13)	C4—H4B	0.9700
Mn1—N3ⁱ	2.2665 (14)	C5—C6	1.382 (3)
Mn1—N3	2.2665 (14)	C5—C7ⁱⁱ	1.384 (2)
Mn1—Cl1ⁱ	2.5639 (4)	C6—C7	1.378 (3)
Mn1—Cl1	2.5639 (4)	C6—H6	0.9300
N1—C3	1.327 (2)	C7—C5ⁱⁱ	1.384 (2)
N1—C1	1.373 (2)	C7—H7	0.9300
N2—C3	1.346 (2)	C8—C9	1.344 (3)
N2—C2	1.373 (2)	C8—H8	0.9300
N2—C4	1.468 (2)	C9—H9	0.9300
N3—C10	1.320 (2)	C10—H10	0.9300
N3—C8	1.375 (2)	C11—C12	1.515 (2)
N4—C10	1.340 (2)	C11—H11A	0.9700
N4—C9	1.373 (2)	C11—H11B	0.9700
N4—C11	1.465 (2)	C12—C14	1.379 (2)
C1—C2	1.351 (2)	C12—C13	1.392 (2)
C1—H1	0.9300	C13—C14ⁱⁱⁱ	1.372 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—H3	0.9300	C14—C13ⁱⁱⁱ	1.372 (2)
C4—C5	1.509 (2)	C14—H14	0.9300

N3ⁱ—Mn1—N3	180.00 (12)	C5—C4—H4A	109.3
N3ⁱ—Mn1—N1ⁱ	86.10 (5)	N2—C4—H4B	109.3
N3—Mn1—N1ⁱ	93.90 (5)	C5—C4—H4B	109.3
N3ⁱ—Mn1—N1	93.90 (5)	H4A—C4—H4B	108.0
N3—Mn1—N1	86.10 (5)	C6—C5—C7ⁱⁱ	118.81 (15)
N1ⁱ—Mn1—N1	180.00 (10)	C6—C5—C4	120.56 (16)
N3ⁱ—Mn1—Cl1ⁱ	90.07 (4)	C7ⁱⁱ—C5—C4	120.62 (16)
N3—Mn1—Cl1ⁱ	89.93 (4)	C7—C6—C5	121.07 (16)
N1ⁱ—Mn1—Cl1ⁱ	89.62 (4)	C7—C6—H6	119.5
N1—Mn1—Cl1ⁱ	90.38 (4)	C5—C6—H6	119.5
N3ⁱ—Mn1—Cl1	89.93 (4)	C6—C7—C5ⁱⁱ	120.11 (18)
N3—Mn1—Cl1	90.07 (4)	C6—C7—H7	119.9
N1ⁱ—Mn1—Cl1	90.38 (4)	C5ⁱⁱ—C7—H7	119.9
N1—Mn1—Cl1	89.62 (4)	C9—C8—N3	109.95 (16)
Cl1ⁱ—Mn1—Cl1	180.00 (2)	C9—C8—H8	125.0
C3—N1—C1	105.16 (14)	N3—C8—H8	125.0
C3—N1—Mn1	126.56 (12)	C8—C9—N4	106.61 (16)
C1—N1—Mn1	124.54 (12)	C8—C9—H9	126.7
C3—N2—C2	107.31 (15)	N4—C9—H9	126.7
C3—N2—C4	125.77 (16)	N3—C10—N4	112.02 (16)
C2—N2—C4	126.68 (15)	N3—C10—H10	124.0
C10—N3—C8	104.94 (15)	N4—C10—H10	124.0
C10—N3—Mn1	124.43 (12)	N4—C11—C12	113.24 (15)
C8—N3—Mn1	130.38 (11)	N4—C11—H11A	108.9
C10—N4—C9	106.47 (14)	C12—C11—H11A	108.9
C10—N4—C11	125.48 (16)	N4—C11—H11B	108.9
C9—N4—C11	127.90 (16)	C12—C11—H11B	108.9
C2—C1—N1	110.37 (17)	H11A—C11—H11B	107.7
C2—C1—H1	124.8	C14—C12—C13	118.21 (15)
N1—C1—H1	124.8	C14—C12—C11	122.95 (15)
C1—C2—N2	105.93 (15)	C13—C12—C11	118.78 (15)
C1—C2—H2	127.0	C14ⁱⁱⁱ—C13—C12	120.25 (16)
N2—C2—H2	127.0	C14ⁱⁱⁱ—C13—H13	119.9
N1—C3—N2	111.22 (16)	C12—C13—H13	119.9
N1—C3—H3	124.4	C13ⁱⁱⁱ—C14—C12	121.54 (15)
N2—C3—H3	124.4	C13ⁱⁱⁱ—C14—H14	119.2
N2—C4—C5	111.57 (15)	C12—C14—H14	119.2
N2—C4—H4A	109.3

N3ⁱ—Mn1—N1—C3	−87.09 (14)	C3—N2—C4—C5	−106.8 (2)
N3—Mn1—N1—C3	92.91 (14)	C2—N2—C4—C5	67.0 (2)
Cl1ⁱ—Mn1—N1—C3	−177.19 (14)	N2—C4—C5—C6	72.4 (2)
Cl1—Mn1—N1—C3	2.81 (14)	N2—C4—C5—C7ⁱⁱ	−106.34 (19)
N3ⁱ—Mn1—N1—C1	118.00 (13)	C7ⁱⁱ—C5—C6—C7	−0.4 (3)
N3—Mn1—N1—C1	−62.00 (13)	C4—C5—C6—C7	−179.12 (18)
Cl1ⁱ—Mn1—N1—C1	27.91 (13)	C5—C6—C7—C5ⁱⁱ	0.4 (3)
Cl1—Mn1—N1—C1	−152.09 (13)	C10—N3—C8—C9	0.2 (2)
N1ⁱ—Mn1—N3—C10	139.92 (14)	Mn1—N3—C8—C9	−174.10 (13)
N1—Mn1—N3—C10	−40.08 (14)	N3—C8—C9—N4	−0.5 (2)
Cl1ⁱ—Mn1—N3—C10	−130.47 (14)	C10—N4—C9—C8	0.5 (2)
Cl1—Mn1—N3—C10	49.53 (14)	C11—N4—C9—C8	176.26 (17)
N1ⁱ—Mn1—N3—C8	−46.74 (16)	C8—N3—C10—N4	0.1 (2)
N1—Mn1—N3—C8	133.26 (16)	Mn1—N3—C10—N4	174.89 (11)
Cl1ⁱ—Mn1—N3—C8	42.87 (15)	C9—N4—C10—N3	−0.4 (2)
Cl1—Mn1—N3—C8	−137.13 (15)	C11—N4—C10—N3	−176.28 (15)
C3—N1—C1—C2	−0.28 (19)	C10—N4—C11—C12	86.3 (2)
Mn1—N1—C1—C2	159.05 (12)	C9—N4—C11—C12	−88.6 (2)
N1—C1—C2—N2	0.6 (2)	N4—C11—C12—C14	−30.7 (2)
C3—N2—C2—C1	−0.67 (19)	N4—C11—C12—C13	152.19 (17)
C4—N2—C2—C1	−175.37 (15)	C14—C12—C13—C14ⁱⁱⁱ	−0.5 (3)
C1—N1—C3—N2	−0.16 (19)	C11—C12—C13—C14ⁱⁱⁱ	176.75 (18)
Mn1—N1—C3—N2	−158.94 (11)	C13—C12—C14—C13ⁱⁱⁱ	0.5 (3)
C2—N2—C3—N1	0.53 (19)	C11—C12—C14—C13ⁱⁱⁱ	−176.62 (19)
C4—N2—C3—N1	175.29 (15)

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N3,N4,C8–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cg^iv	0.97	2.65	3.522 (2)	150

Symmetry code: (iv) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₄H₁₄N₄)₂]
M_r	602.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7812 (2), 12.7910 (3), 14.2575 (4)
β (°)	105.539 (3)
V (Å³)	1367.17 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.21 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.865, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	3921, 2367, 2102
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.093, 1.04
No. of reflections	2367
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2010).

Selected bond lengths (Å) top

Mn1—N1	2.2695 (13)	Mn1—Cl1	2.5639 (4)
Mn1—N3	2.2665 (14)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N3,N4,C8–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cgⁱ	0.97	2.65	3.522 (2)	150

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province (No. 2010 A140009) and the International Technology Cooperation Project of Science and Technology Department of Henan Province of China (No. 104300510044).

References

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Volume 67| Part 8| August 2011| Page m1156

doi:10.1107/S1600536811029485

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