Dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine)manganese(II)

Ha, K.

doi:10.1107/S1600536810004204

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m262

doi:10.1107/S1600536810004204

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Dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine)manganese(II)

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 30 January 2010; accepted 2 February 2010; online 6 February 2010)

In the title complex, [MnCl₂(C₁₈H₁₂N₆)], the Mn^II ion is five-coordinated in an approximately square-pyramidal geometry defined by three N atoms of the tridentate 2,4,6-tri-2-pyridyl-1,3,5-triazine ligand and two Cl atoms. In the crystal, the molecules are stacked in columns along the c axis and display intermolecular π–π interactions between the six-membered rings, the shortest centroid–centroid distance being 3.553 (3)Å. Intermolecular C—H⋯Cl contacts are also noted.

Related literature

For the crystal structure of 2,4,6-tri-2-pyridyl-1,3,5-triazine (tptz), see: Drew et al. (1998 ). For the crystal structures of some other Mn(II)–tptz complexes, see: Hsu et al. (2006 ); Majumder et al. (2006 ); Sun et al. (2007 ); Tyagi & Singh (2009 ); Zhang et al. (2008 ); Zhao et al. (2007 ).

Experimental

Crystal data

[MnCl₂(C₁₈H₁₂N₆)]
M_r = 438.18
Triclinic, $[P \overline 1]$
a = 8.8247 (7) Å
b = 10.5538 (9) Å
c = 10.9635 (9) Å
α = 66.572 (2)°
β = 75.812 (2)°
γ = 82.867 (2)°
V = 907.91 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 200 K
0.32 × 0.13 × 0.06 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.856, T_max = 1.000
6800 measured reflections
4424 independent reflections
2256 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.163
S = 1.05
4424 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cl1ⁱ	0.95	2.77	3.594 (5)	145
C15—H15⋯Cl1ⁱⁱ	0.95	2.82	3.714 (5)	157
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004204/tk2624sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004204/tk2624Isup2.hkl

checkCIF report

Comment top

Since the original structure determination of 2,4,6-tri-2-pyridyl-1,3,5-triazine ligand (Drew et al., 1998), triazine complexes, including Mn(II) derivatives, have attracted considerable interest over the years (Hsu et al., 2006; Majumder et al., 2006; Sun et al., 2007; Tyagi & Singh, 2009; Zhang et al., 2008; Zhao et al., 2007). In the title complex, [MnCl₂(C₁₈H₁₂N₆)], the Mn^II ion is five-coordinated in an approximately square-pyramidal geometry by three N atoms of the tridentate 2,4,6-tri-2-pyridyl-1,3,5-triazine ligand and two Cl atoms (Fig. 1). While the Mn—Cl bond lengths are almost equal [2.3345 (16) and 2.3494 (16) Å], the Mn—N bond lengths appear to be different (Table 1). The Mn—N(pyridyl) bonds [2.303 (4) and 2.324 (4) Å] tend to be slightly longer than the Mn—N(triazine) bond (2.197 (4) Å]. The N—Mn—N chelating angles are 70.05 (13)° and 70.68 (14)°, and the Cl—Mn—Cl bond angle is 112.22 (6) °. The molecules are stacked in columns along the c axis and display intermolecular π-π interactions between the six-membered rings, with a shortest centroid-centroid distance of 3.553 (3) Å, and weak intermolecular C—H···Cl contacts (Fig. 2 and Table 2).

Related literature top

For the crystal structure of 2,4,6-tri-2-pyridyl-1,3,5-triazine (tptz), see: Drew et al. (1998). For the crystal structures of some other Mn(II)–tptz complexes, see: Hsu et al. (2006); Majumder et al. (2006); Sun et al. (2007); Tyagi & Singh (2009); Zhang et al. (2008); Zhao et al. (2007).

Experimental top

To a solution of 2,4,6-tri-2-pyridyl-1,3,5-triazine (0.25 g, 0.80 mmol) in EtOH (30 ml) was added MnCl₂.4H₂O (0.16 g, 0.81 mmol) and stirred for 2 h at room temperature. The formed precipitate was separated by filtration and washed with EtOH and dried under vacuum, to give a yellow powder (0.14 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a CH₃CN solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex, with displacement ellipsoids drawn at the 50% probability level for non-H atoms.
	Fig. 2. View of the unit-cell contents of the title complex. Hydrogen-bond interactions are drawn with dashed lines.

Dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine)manganese(II) top

Crystal data top

[MnCl₂(C₁₈H₁₂N₆)]	Z = 2
M_r = 438.18	F(000) = 442
Triclinic, P1	D_x = 1.603 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8247 (7) Å	Cell parameters from 1442 reflections
b = 10.5538 (9) Å	θ = 2.3–24.8°
c = 10.9635 (9) Å	µ = 1.04 mm⁻¹
α = 66.572 (2)°	T = 200 K
β = 75.812 (2)°	Plate, yellow
γ = 82.867 (2)°	0.32 × 0.13 × 0.06 mm
V = 907.91 (13) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	4424 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→11
T_min = 0.856, T_max = 1.000	k = −14→12
6800 measured reflections	l = −14→14

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0495P)² + 0.2689P] where P = (F_o² + 2F_c²)/3
4424 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

[MnCl₂(C₁₈H₁₂N₆)]	γ = 82.867 (2)°
M_r = 438.18	V = 907.91 (13) Å³
Triclinic, P1	Z = 2
a = 8.8247 (7) Å	Mo Kα radiation
b = 10.5538 (9) Å	µ = 1.04 mm⁻¹
c = 10.9635 (9) Å	T = 200 K
α = 66.572 (2)°	0.32 × 0.13 × 0.06 mm
β = 75.812 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4424 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2256 reflections with I > 2σ(I)
T_min = 0.856, T_max = 1.000	R_int = 0.049
6800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	Δρ_max = 0.73 e Å⁻³
4424 reflections	Δρ_min = −0.86 e Å⁻³
244 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.11311 (8)	−0.09650 (8)	0.20984 (8)	0.0315 (2)
Cl1	1.19313 (15)	−0.18383 (16)	0.41816 (14)	0.0489 (4)
Cl2	1.27174 (15)	−0.17981 (15)	0.05186 (14)	0.0474 (4)
N1	0.8963 (4)	0.0276 (4)	0.2302 (4)	0.0273 (9)
N2	0.7690 (4)	0.2386 (4)	0.2287 (4)	0.0275 (9)
N3	0.6232 (4)	0.0355 (4)	0.2991 (4)	0.0280 (9)
N4	1.1690 (4)	0.1343 (4)	0.1225 (4)	0.0293 (10)
N5	0.4828 (5)	0.3769 (4)	0.2798 (4)	0.0368 (11)
N6	0.9004 (5)	−0.2292 (4)	0.2531 (4)	0.0323 (10)
C1	0.8958 (5)	0.1617 (5)	0.2043 (5)	0.0251 (11)
C2	1.0526 (5)	0.2239 (5)	0.1442 (5)	0.0264 (11)
C3	1.0755 (6)	0.3612 (5)	0.1080 (5)	0.0311 (12)
H3	0.9909	0.4206	0.1266	0.037*
C4	1.2251 (6)	0.4128 (5)	0.0433 (5)	0.0360 (13)
H4	1.2443	0.5077	0.0165	0.043*
C5	1.3438 (6)	0.3223 (5)	0.0196 (5)	0.0395 (14)
H5	1.4465	0.3543	−0.0251	0.047*
C6	1.3123 (6)	0.1852 (5)	0.0613 (5)	0.0355 (13)
H6	1.3959	0.1235	0.0459	0.043*
C7	0.6341 (5)	0.1688 (5)	0.2782 (5)	0.0268 (11)
C8	0.4833 (5)	0.2407 (5)	0.3123 (5)	0.0284 (11)
C9	0.3490 (5)	0.1626 (5)	0.3722 (5)	0.0324 (12)
H9	0.3537	0.0668	0.3893	0.039*
C10	0.2098 (6)	0.2279 (6)	0.4058 (5)	0.0405 (14)
H10	0.1164	0.1774	0.4479	0.049*
C11	0.2074 (6)	0.3662 (6)	0.3781 (6)	0.0446 (14)
H11	0.1130	0.4128	0.4028	0.053*
C12	0.3452 (6)	0.4377 (6)	0.3130 (6)	0.0419 (14)
H12	0.3416	0.5345	0.2909	0.050*
C13	0.7563 (5)	−0.0299 (5)	0.2721 (5)	0.0278 (11)
C14	0.7581 (5)	−0.1748 (5)	0.2860 (5)	0.0272 (11)
C15	0.6218 (6)	−0.2477 (5)	0.3296 (5)	0.0337 (12)
H15	0.5226	−0.2055	0.3503	0.040*
C16	0.6351 (6)	−0.3834 (6)	0.3417 (6)	0.0429 (14)
H16	0.5445	−0.4373	0.3741	0.051*
C17	0.7807 (6)	−0.4417 (6)	0.3066 (6)	0.0428 (14)
H17	0.7919	−0.5348	0.3131	0.051*
C18	0.9087 (6)	−0.3594 (5)	0.2619 (5)	0.0379 (13)
H18	1.0086	−0.3977	0.2359	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0200 (4)	0.0324 (5)	0.0388 (5)	0.0006 (3)	−0.0039 (3)	−0.0120 (4)
Cl1	0.0270 (8)	0.0674 (11)	0.0416 (8)	−0.0058 (7)	−0.0071 (6)	−0.0086 (7)
Cl2	0.0349 (8)	0.0593 (10)	0.0476 (9)	0.0063 (7)	−0.0022 (6)	−0.0259 (7)
N1	0.017 (2)	0.028 (2)	0.036 (2)	−0.0024 (16)	−0.0035 (17)	−0.0133 (19)
N2	0.022 (2)	0.029 (2)	0.033 (2)	−0.0064 (17)	−0.0035 (17)	−0.0136 (19)
N3	0.018 (2)	0.028 (2)	0.037 (2)	−0.0030 (17)	−0.0009 (17)	−0.0132 (19)
N4	0.017 (2)	0.032 (2)	0.033 (2)	−0.0043 (17)	0.0016 (17)	−0.0104 (19)
N5	0.026 (2)	0.035 (3)	0.052 (3)	0.0091 (19)	−0.012 (2)	−0.020 (2)
N6	0.027 (2)	0.028 (2)	0.045 (3)	0.0023 (18)	−0.0091 (19)	−0.017 (2)
C1	0.020 (3)	0.019 (3)	0.032 (3)	−0.0023 (19)	−0.002 (2)	−0.007 (2)
C2	0.015 (2)	0.031 (3)	0.033 (3)	−0.001 (2)	−0.004 (2)	−0.012 (2)
C3	0.028 (3)	0.024 (3)	0.039 (3)	−0.004 (2)	−0.007 (2)	−0.008 (2)
C4	0.027 (3)	0.036 (3)	0.040 (3)	−0.013 (2)	−0.006 (2)	−0.006 (2)
C5	0.026 (3)	0.041 (4)	0.042 (3)	−0.009 (2)	−0.005 (2)	−0.007 (3)
C6	0.021 (3)	0.039 (3)	0.041 (3)	−0.002 (2)	0.001 (2)	−0.014 (3)
C7	0.021 (3)	0.029 (3)	0.030 (3)	−0.001 (2)	−0.005 (2)	−0.012 (2)
C8	0.024 (3)	0.030 (3)	0.030 (3)	0.000 (2)	−0.006 (2)	−0.010 (2)
C9	0.023 (3)	0.036 (3)	0.034 (3)	−0.001 (2)	−0.005 (2)	−0.009 (2)
C10	0.024 (3)	0.054 (4)	0.037 (3)	0.004 (3)	−0.005 (2)	−0.014 (3)
C11	0.032 (3)	0.059 (4)	0.044 (3)	0.014 (3)	−0.015 (3)	−0.022 (3)
C12	0.045 (4)	0.040 (3)	0.050 (4)	0.010 (3)	−0.020 (3)	−0.023 (3)
C13	0.018 (3)	0.033 (3)	0.030 (3)	−0.007 (2)	−0.002 (2)	−0.009 (2)
C14	0.024 (3)	0.026 (3)	0.033 (3)	−0.003 (2)	−0.006 (2)	−0.012 (2)
C15	0.026 (3)	0.035 (3)	0.040 (3)	−0.006 (2)	−0.003 (2)	−0.015 (3)
C16	0.042 (4)	0.036 (3)	0.053 (4)	−0.015 (3)	−0.004 (3)	−0.017 (3)
C17	0.045 (4)	0.032 (3)	0.052 (4)	−0.008 (3)	−0.005 (3)	−0.018 (3)
C18	0.041 (3)	0.027 (3)	0.052 (4)	0.006 (2)	−0.012 (3)	−0.022 (3)

Geometric parameters (Å, º) top

Mn1—N1	2.197 (4)	C4—H4	0.9500
Mn1—N4	2.303 (4)	C5—C6	1.376 (7)
Mn1—N6	2.324 (4)	C5—H5	0.9500
Mn1—Cl2	2.3345 (16)	C6—H6	0.9500
Mn1—Cl1	2.3494 (16)	C7—C8	1.490 (6)
N1—C1	1.329 (6)	C8—C9	1.395 (6)
N1—C13	1.339 (5)	C9—C10	1.375 (7)
N2—C1	1.335 (6)	C9—H9	0.9500
N2—C7	1.355 (5)	C10—C11	1.367 (7)
N3—C13	1.317 (6)	C10—H10	0.9500
N3—C7	1.345 (6)	C11—C12	1.390 (7)
N4—C6	1.343 (5)	C11—H11	0.9500
N4—C2	1.351 (6)	C12—H12	0.9500
N5—C8	1.336 (6)	C13—C14	1.474 (6)
N5—C12	1.339 (6)	C14—C15	1.386 (6)
N6—C18	1.332 (6)	C15—C16	1.378 (7)
N6—C14	1.342 (6)	C15—H15	0.9500
C1—C2	1.488 (6)	C16—C17	1.388 (7)
C2—C3	1.369 (6)	C16—H16	0.9500
C3—C4	1.398 (6)	C17—C18	1.380 (7)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.375 (7)	C18—H18	0.9500

N1—Mn1—N4	70.05 (13)	N4—C6—H6	118.4
N1—Mn1—N6	70.68 (14)	C5—C6—H6	118.4
N4—Mn1—N6	137.65 (14)	N3—C7—N2	124.9 (4)
N1—Mn1—Cl2	139.00 (11)	N3—C7—C8	115.2 (4)
N4—Mn1—Cl2	104.03 (11)	N2—C7—C8	119.9 (4)
N6—Mn1—Cl2	95.27 (11)	N5—C8—C9	123.6 (5)
N1—Mn1—Cl1	108.53 (11)	N5—C8—C7	118.4 (4)
N4—Mn1—Cl1	103.39 (11)	C9—C8—C7	118.0 (4)
N6—Mn1—Cl1	103.49 (11)	C10—C9—C8	118.3 (5)
Cl2—Mn1—Cl1	112.22 (6)	C10—C9—H9	120.9
C1—N1—C13	116.3 (4)	C8—C9—H9	120.9
C1—N1—Mn1	122.6 (3)	C11—C10—C9	119.2 (5)
C13—N1—Mn1	121.1 (3)	C11—C10—H10	120.4
C1—N2—C7	113.9 (4)	C9—C10—H10	120.4
C13—N3—C7	115.7 (4)	C10—C11—C12	118.9 (5)
C6—N4—C2	117.2 (4)	C10—C11—H11	120.5
C6—N4—Mn1	124.6 (3)	C12—C11—H11	120.5
C2—N4—Mn1	117.9 (3)	N5—C12—C11	123.3 (5)
C8—N5—C12	116.7 (4)	N5—C12—H12	118.3
C18—N6—C14	117.5 (4)	C11—C12—H12	118.3
C18—N6—Mn1	125.3 (3)	N3—C13—N1	123.9 (5)
C14—N6—Mn1	116.8 (3)	N3—C13—C14	120.5 (4)
N1—C1—N2	125.0 (4)	N1—C13—C14	115.6 (4)
N1—C1—C2	114.3 (4)	N6—C14—C15	123.3 (5)
N2—C1—C2	120.8 (4)	N6—C14—C13	114.9 (4)
N4—C2—C3	123.0 (4)	C15—C14—C13	121.8 (4)
N4—C2—C1	114.0 (4)	C16—C15—C14	117.7 (5)
C3—C2—C1	122.9 (4)	C16—C15—H15	121.1
C2—C3—C4	119.1 (5)	C14—C15—H15	121.1
C2—C3—H3	120.5	C15—C16—C17	120.2 (5)
C4—C3—H3	120.5	C15—C16—H16	119.9
C5—C4—C3	118.2 (5)	C17—C16—H16	119.9
C5—C4—H4	120.9	C18—C17—C16	117.4 (5)
C3—C4—H4	120.9	C18—C17—H17	121.3
C4—C5—C6	119.4 (5)	C16—C17—H17	121.3
C4—C5—H5	120.3	N6—C18—C17	123.8 (5)
C6—C5—H5	120.3	N6—C18—H18	118.1
N4—C6—C5	123.1 (5)	C17—C18—H18	118.1

N4—Mn1—N1—C1	−8.9 (3)	C3—C4—C5—C6	−0.8 (8)
N6—Mn1—N1—C1	−172.7 (4)	C2—N4—C6—C5	−0.6 (7)
Cl2—Mn1—N1—C1	−97.5 (4)	Mn1—N4—C6—C5	−174.8 (4)
Cl1—Mn1—N1—C1	89.0 (4)	C4—C5—C6—N4	1.3 (8)
N4—Mn1—N1—C13	172.3 (4)	C13—N3—C7—N2	2.1 (7)
N6—Mn1—N1—C13	8.4 (3)	C13—N3—C7—C8	−178.6 (4)
Cl2—Mn1—N1—C13	83.7 (4)	C1—N2—C7—N3	−1.6 (7)
Cl1—Mn1—N1—C13	−89.8 (4)	C1—N2—C7—C8	179.0 (4)
N1—Mn1—N4—C6	−176.4 (4)	C12—N5—C8—C9	2.8 (7)
N6—Mn1—N4—C6	−153.5 (4)	C12—N5—C8—C7	−179.5 (4)
Cl2—Mn1—N4—C6	−39.0 (4)	N3—C7—C8—N5	−172.6 (4)
Cl1—Mn1—N4—C6	78.4 (4)	N2—C7—C8—N5	6.8 (7)
N1—Mn1—N4—C2	9.4 (3)	N3—C7—C8—C9	5.2 (6)
N6—Mn1—N4—C2	32.4 (4)	N2—C7—C8—C9	−175.4 (4)
Cl2—Mn1—N4—C2	146.9 (3)	N5—C8—C9—C10	−3.3 (7)
Cl1—Mn1—N4—C2	−95.7 (3)	C7—C8—C9—C10	179.0 (4)
N1—Mn1—N6—C18	178.9 (4)	C8—C9—C10—C11	0.8 (7)
N4—Mn1—N6—C18	156.1 (4)	C9—C10—C11—C12	1.8 (8)
Cl2—Mn1—N6—C18	38.5 (4)	C8—N5—C12—C11	0.1 (7)
Cl1—Mn1—N6—C18	−75.9 (4)	C10—C11—C12—N5	−2.4 (8)
N1—Mn1—N6—C14	−8.5 (3)	C7—N3—C13—N1	1.9 (7)
N4—Mn1—N6—C14	−31.4 (5)	C7—N3—C13—C14	−177.6 (4)
Cl2—Mn1—N6—C14	−148.9 (3)	C1—N1—C13—N3	−5.8 (7)
Cl1—Mn1—N6—C14	96.7 (3)	Mn1—N1—C13—N3	173.0 (4)
C13—N1—C1—N2	6.4 (7)	C1—N1—C13—C14	173.7 (4)
Mn1—N1—C1—N2	−172.5 (4)	Mn1—N1—C13—C14	−7.5 (5)
C13—N1—C1—C2	−173.8 (4)	C18—N6—C14—C15	0.8 (7)
Mn1—N1—C1—C2	7.3 (5)	Mn1—N6—C14—C15	−172.4 (4)
C7—N2—C1—N1	−2.8 (7)	C18—N6—C14—C13	−179.0 (4)
C7—N2—C1—C2	177.4 (4)	Mn1—N6—C14—C13	7.8 (5)
C6—N4—C2—C3	−0.7 (7)	N3—C13—C14—N6	178.8 (4)
Mn1—N4—C2—C3	173.9 (4)	N1—C13—C14—N6	−0.7 (6)
C6—N4—C2—C1	176.3 (4)	N3—C13—C14—C15	−1.0 (7)
Mn1—N4—C2—C1	−9.1 (5)	N1—C13—C14—C15	179.5 (4)
N1—C1—C2—N4	1.6 (6)	N6—C14—C15—C16	1.3 (8)
N2—C1—C2—N4	−178.5 (4)	C13—C14—C15—C16	−178.9 (4)
N1—C1—C2—C3	178.6 (4)	C14—C15—C16—C17	−2.1 (8)
N2—C1—C2—C3	−1.6 (7)	C15—C16—C17—C18	0.9 (8)
N4—C2—C3—C4	1.2 (7)	C14—N6—C18—C17	−2.1 (8)
C1—C2—C3—C4	−175.5 (4)	Mn1—N6—C18—C17	170.4 (4)
C2—C3—C4—C5	−0.4 (7)	C16—C17—C18—N6	1.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.95	2.77	3.594 (5)	145
C15—H15···Cl1ⁱⁱ	0.95	2.82	3.714 (5)	157

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

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₈H₁₂N₆)]
M_r	438.18
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	8.8247 (7), 10.5538 (9), 10.9635 (9)
α, β, γ (°)	66.572 (2), 75.812 (2), 82.867 (2)
V (Å³)	907.91 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.32 × 0.13 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.856, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6800, 4424, 2256
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.163, 1.05
No. of reflections	4424
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.86

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.95	2.77	3.594 (5)	145
C15—H15···Cl1ⁱⁱ	0.95	2.82	3.714 (5)	157

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

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009–0094056).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Drew, M. G. B., Hudson, M. J., Iveson, P. B., Russell, M. L. & Madic, C. (1998). Acta Cryst. C54, 985–987. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hsu, G.-Y., Misra, P., Cheng, S.-C., Wei, H.-H. & Mohanta, S. (2006). Polyhedron, 25, 3393–3398. Web of Science CSD CrossRef CAS Google Scholar
Majumder, A., Pilet, G., Rodriguez, M. T. G. & Misra, P. (2006). Polyhedron, 25, 2550–2558. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X.-P., Gu, W. & Liu, X. (2007). Acta Cryst. E63, m1027–m1028. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tyagi, P. & Singh, U. P. (2009). J. Coord. Chem. 62, 1613–1622. Web of Science CSD CrossRef CAS Google Scholar
Zhang, M., Fang, R. & Zhao, Q. (2008). J. Chem. Crystallogr. 38, 601–604. Web of Science CSD CrossRef CAS Google Scholar
Zhao, H., Shatruk, M., Prosvirin, A. V. & Dunbar, K. R. (2007). Chem. Eur. J. 13, 6573–6589. Web of Science CSD CrossRef PubMed CAS Google Scholar