A monoclinic polymorph of dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)manganese(II)

Ha, K.

doi:10.1107/S1600536811034118

metal-organic compounds

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Volume 67| Part 9| September 2011| Page m1306

doi:10.1107/S1600536811034118

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A monoclinic polymorph of dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ³N²,N¹,N⁶)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 10 August 2011; accepted 20 August 2011; online 27 August 2011)

The Mn^II ion in the title complex, [MnCl₂(C₁₈H₁₂N₆)], is five-coordinated in a distorted square-pyramidal geometry by three N atoms of the tridentate 2,4,6-tri-2-pyridyl-1,3,5-triazine ligand and two chloride anions. In the crystal, the pyridyl rings are located approximately parallel to their carrier triazine ring, making dihedral angles of 5.0 (1), 3.8 (1) and 3.2 (1)°. Intramolecular C—H⋯N hydrogen bonds are present. The complexes are stacked in columns along the c axis and linked by intermolecular C—H⋯Cl hydrogen bonds, forming one-dimensional chains. In the column, intermolecular π–π interactions between the six-membered rings are present, the shortest centroid–centroid distance being 3.623 (2) Å. The structure reported herein represents a monoclinic polymorph of the previously reported triclinic form [Ha (2010 ). Acta Cryst. E66, m262].

Related literature

For the triclinic crystal structure of the title complex, see: Ha (2010).

Experimental

Crystal data

[MnCl₂(C₁₈H₁₂N₆)]
M_r = 438.18
Monoclinic, P 2₁ /c
a = 10.8799 (9) Å
b = 19.5524 (16) Å
c = 8.6446 (7) Å
β = 101.051 (2)°
V = 1804.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 200 K
0.29 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.826, T_max = 1.000
13299 measured reflections
4450 independent reflections
2653 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.01
4450 reflections
292 parameters
All H-atom parameters refined
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—N1	2.189 (2)
Mn1—N4	2.318 (2)
Mn1—N6	2.348 (2)
Mn1—Cl1	2.3470 (10)
Mn1—Cl2	2.3400 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cl1ⁱ	0.91 (3)	2.76 (3)	3.589 (3)	151 (3)
C15—H15⋯Cl1ⁱⁱ	0.92 (3)	2.81 (3)	3.633 (4)	151 (2)
C3—H3⋯N2	0.97 (3)	2.52 (3)	2.896 (4)	103 (2)
C9—H9⋯N3	0.92 (3)	2.41 (3)	2.735 (4)	101 (2)
C15—H15⋯N3	0.92 (3)	2.57 (3)	2.869 (4)	100 (2)
Symmetry codes: (i) -x+2, -y, -z+2; (ii) x, y, z+1.

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 datablock global. DOI: 10.1107/S1600536811034118/hp2014sup1.cif

checkCIF report

Comment top

The crystal structure of the title complex, [MnCl₂(tptz)] (tptz = 2,4,6-tri-2-pyridyl-1,3,5-triazine, C₁₈H₁₂N₆), was previously reported in the triclinic space group P1 (Ha, 2010). The structure presented herein is essentially the same as the published structure and represents a monoclinic polymorph.

The Mn^II ion in the complex is five-coordinated in an approximately square-pyramidal geometry by three N atoms of the tridentate tptz ligand and two chloride anions (Fig. 1). While the Mn—Cl bond lengths are almost equal, the Mn—N bond lengths are somewhat different (Table 1). The Mn1—N4/6(pyridyl) bonds are slightly longer than the Mn1—N1(triazine) bond. In the crystal, the pyridyl rings are located approximately parallel to their carrier triazine ring, making dihedral angles of 5.0 (1)°, 3.8 (1)° and 3.2 (1)°. The complexes are stacked in columns along the c axis and linked by intermolecular C—H···Cl hydrogen bonds, forming one-dimensional chains (Fig. 2 and Table 2). There are also intramolecular C—H···N hydrogen bonds (Table 2). In the column, intermolecular π-π interactions between the six-membered rings are present, the shortest centroid-centroid distance being 3.623 (2) Å.

Related literature top

For the triclinic crystal structure of the title complex, see: Ha (2010).

Experimental top

To a solution of MnCl₂.4H₂O (0.2969 g, 1.50 mmol) in MeOH (30 ml) was added 2,4,6-tri-2-pyridyl-1,3,5-triazine (0.1561 g, 0.50 mmol) and stirred for 3 h at room temperature. The formed precipitate was separated by filtration and washed with MeOH and dried at 50 °C, to give a yellow powder (0.1355 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an N,N-dimethylformamide (DMF) solution at 60 °C.

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. Intermolecular hydrogen-bond interactions are drawn with dashed lines.

dichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine- κ³N²,N¹,N⁶)manganese(II) top

Crystal data top

[MnCl₂(C₁₈H₁₂N₆)]	F(000) = 884
M_r = 438.18	D_x = 1.613 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3437 reflections
a = 10.8799 (9) Å	θ = 2.6–28.0°
b = 19.5524 (16) Å	µ = 1.04 mm⁻¹
c = 8.6446 (7) Å	T = 200 K
β = 101.051 (2)°	Stick, yellow
V = 1804.8 (3) Å³	0.29 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	4450 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→13
T_min = 0.826, T_max = 1.000	k = −26→21
13299 measured reflections	l = −11→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0443P)²] where P = (F_o² + 2F_c²)/3
4450 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[MnCl₂(C₁₈H₁₂N₆)]	V = 1804.8 (3) Å³
M_r = 438.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8799 (9) Å	µ = 1.04 mm⁻¹
b = 19.5524 (16) Å	T = 200 K
c = 8.6446 (7) Å	0.29 × 0.15 × 0.15 mm
β = 101.051 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4450 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2653 reflections with I > 2σ(I)
T_min = 0.826, T_max = 1.000	R_int = 0.056
13299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	All H-atom parameters refined
S = 1.01	Δρ_max = 0.52 e Å⁻³
4450 reflections	Δρ_min = −0.56 e Å⁻³
292 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	0.67220 (5)	−0.04692 (2)	0.39757 (5)	0.02899 (15)
Cl1	0.85416 (9)	−0.08835 (5)	0.32140 (10)	0.0471 (3)
Cl2	0.49434 (8)	−0.09448 (4)	0.23876 (10)	0.0428 (2)
N1	0.7359 (2)	0.01546 (12)	0.6079 (3)	0.0259 (6)
N2	0.8167 (2)	0.12055 (12)	0.7203 (3)	0.0266 (6)
N3	0.8117 (2)	0.02159 (12)	0.8809 (3)	0.0279 (6)
N4	0.6701 (2)	0.06745 (12)	0.3264 (3)	0.0279 (6)
N5	0.9360 (2)	0.18914 (13)	0.9898 (3)	0.0324 (6)
N6	0.6586 (2)	−0.11029 (12)	0.6245 (3)	0.0277 (6)
C1	0.7629 (3)	0.08207 (14)	0.5988 (3)	0.0256 (7)
C2	0.7235 (3)	0.11228 (15)	0.4397 (3)	0.0255 (7)
C3	0.7402 (3)	0.18052 (16)	0.4105 (4)	0.0286 (7)
H3	0.783 (3)	0.2070 (16)	0.499 (4)	0.046 (10)*
C4	0.7004 (3)	0.20518 (17)	0.2583 (4)	0.0340 (8)
H4	0.710 (3)	0.2521 (15)	0.233 (4)	0.034 (9)*
C5	0.6451 (3)	0.16038 (17)	0.1432 (4)	0.0342 (8)
H5	0.614 (3)	0.1737 (14)	0.039 (4)	0.029 (8)*
C6	0.6321 (3)	0.09226 (17)	0.1815 (4)	0.0326 (8)
H6	0.595 (3)	0.0583 (15)	0.109 (4)	0.036 (9)*
C7	0.8439 (3)	0.08676 (14)	0.8588 (3)	0.0249 (7)
C8	0.9099 (3)	0.12252 (15)	1.0019 (3)	0.0259 (7)
C9	0.9396 (3)	0.08632 (17)	1.1435 (4)	0.0304 (7)
H9	0.922 (3)	0.0405 (14)	1.147 (3)	0.027 (8)*
C10	0.9995 (3)	0.12008 (19)	1.2765 (4)	0.0352 (8)
H10	1.016 (3)	0.0986 (15)	1.372 (4)	0.041 (10)*
C11	1.0281 (3)	0.18794 (18)	1.2663 (4)	0.0354 (8)
H11	1.067 (3)	0.2127 (17)	1.357 (4)	0.057 (11)*
C12	0.9943 (3)	0.22022 (18)	1.1217 (4)	0.0358 (8)
H12	1.007 (3)	0.2657 (15)	1.110 (3)	0.026 (8)*
C13	0.7578 (3)	−0.01119 (14)	0.7514 (4)	0.0268 (7)
C14	0.7155 (3)	−0.08276 (14)	0.7630 (3)	0.0261 (7)
C15	0.7327 (3)	−0.11732 (17)	0.9051 (4)	0.0328 (8)
H15	0.779 (3)	−0.0970 (15)	0.993 (4)	0.042 (10)*
C16	0.6929 (3)	−0.18411 (18)	0.9038 (4)	0.0413 (9)
H16	0.699 (3)	−0.2114 (16)	0.992 (4)	0.046 (10)*
C17	0.6338 (3)	−0.21370 (17)	0.7629 (4)	0.0384 (8)
H17	0.606 (3)	−0.2621 (15)	0.760 (3)	0.035 (9)*
C18	0.6168 (3)	−0.17449 (16)	0.6269 (4)	0.0322 (7)
H18	0.567 (3)	−0.1904 (15)	0.528 (4)	0.033 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0372 (3)	0.0270 (3)	0.0217 (3)	0.0009 (2)	0.0029 (2)	−0.0030 (2)
Cl1	0.0452 (6)	0.0684 (7)	0.0269 (5)	0.0200 (4)	0.0046 (4)	0.0010 (4)
Cl2	0.0392 (5)	0.0497 (6)	0.0354 (5)	−0.0031 (4)	−0.0029 (4)	−0.0097 (4)
N1	0.0348 (15)	0.0224 (13)	0.0199 (13)	0.0009 (11)	0.0035 (11)	−0.0001 (10)
N2	0.0296 (15)	0.0277 (14)	0.0218 (13)	0.0020 (11)	0.0028 (11)	−0.0001 (11)
N3	0.0363 (16)	0.0248 (14)	0.0213 (13)	0.0008 (11)	0.0023 (12)	−0.0017 (11)
N4	0.0333 (16)	0.0282 (14)	0.0206 (14)	−0.0012 (11)	0.0013 (11)	−0.0014 (11)
N5	0.0366 (17)	0.0307 (15)	0.0277 (15)	−0.0004 (12)	0.0006 (12)	−0.0028 (12)
N6	0.0339 (16)	0.0255 (14)	0.0228 (14)	0.0029 (11)	0.0033 (11)	−0.0021 (11)
C1	0.0284 (17)	0.0246 (17)	0.0234 (16)	−0.0004 (13)	0.0038 (13)	−0.0024 (12)
C2	0.0293 (17)	0.0269 (17)	0.0205 (15)	0.0014 (13)	0.0053 (13)	−0.0006 (12)
C3	0.0315 (18)	0.0301 (18)	0.0225 (16)	−0.0002 (14)	0.0007 (14)	−0.0017 (13)
C4	0.044 (2)	0.0272 (19)	0.0319 (19)	0.0023 (15)	0.0090 (16)	0.0064 (14)
C5	0.042 (2)	0.040 (2)	0.0195 (17)	0.0028 (15)	0.0020 (15)	0.0034 (14)
C6	0.041 (2)	0.035 (2)	0.0206 (17)	0.0009 (15)	0.0028 (15)	−0.0031 (14)
C7	0.0252 (17)	0.0241 (17)	0.0244 (16)	0.0034 (12)	0.0020 (13)	−0.0003 (12)
C8	0.0254 (17)	0.0277 (17)	0.0231 (16)	0.0052 (13)	0.0005 (13)	−0.0004 (13)
C9	0.0343 (19)	0.0307 (19)	0.0262 (18)	0.0032 (14)	0.0054 (15)	0.0015 (14)
C10	0.036 (2)	0.048 (2)	0.0194 (18)	0.0072 (16)	0.0010 (15)	0.0007 (15)
C11	0.032 (2)	0.047 (2)	0.0252 (18)	0.0034 (15)	0.0009 (15)	−0.0096 (16)
C12	0.037 (2)	0.031 (2)	0.038 (2)	−0.0018 (15)	0.0029 (16)	−0.0084 (16)
C13	0.0296 (17)	0.0247 (16)	0.0266 (17)	0.0030 (13)	0.0064 (14)	−0.0035 (13)
C14	0.0354 (19)	0.0230 (16)	0.0206 (16)	0.0019 (13)	0.0070 (14)	0.0004 (12)
C15	0.040 (2)	0.0314 (19)	0.0258 (18)	−0.0030 (15)	0.0039 (16)	−0.0002 (14)
C16	0.057 (3)	0.035 (2)	0.035 (2)	−0.0046 (17)	0.0146 (18)	0.0102 (17)
C17	0.052 (2)	0.0285 (19)	0.036 (2)	−0.0064 (16)	0.0116 (18)	0.0007 (15)
C18	0.036 (2)	0.0303 (19)	0.0302 (19)	−0.0014 (14)	0.0053 (15)	−0.0069 (14)

Geometric parameters (Å, º) top

Mn1—N1	2.189 (2)	C4—H4	0.95 (3)
Mn1—N4	2.318 (2)	C5—C6	1.386 (4)
Mn1—N6	2.348 (2)	C5—H5	0.93 (3)
Mn1—Cl1	2.3470 (10)	C6—H6	0.95 (3)
Mn1—Cl2	2.3400 (10)	C7—C8	1.481 (4)
N1—C13	1.324 (4)	C8—C9	1.397 (4)
N1—C1	1.341 (3)	C9—C10	1.377 (4)
N2—C1	1.333 (4)	C9—H9	0.92 (3)
N2—C7	1.349 (4)	C10—C11	1.369 (5)
N3—C13	1.325 (4)	C10—H10	0.91 (3)
N3—C7	1.345 (4)	C11—C12	1.386 (5)
N4—C6	1.333 (4)	C11—H11	0.95 (4)
N4—C2	1.359 (4)	C12—H12	0.91 (3)
N5—C12	1.340 (4)	C13—C14	1.483 (4)
N5—C8	1.341 (4)	C14—C15	1.383 (4)
N6—C18	1.337 (4)	C15—C16	1.375 (4)
N6—C14	1.350 (4)	C15—H15	0.92 (3)
C1—C2	1.483 (4)	C16—C17	1.390 (5)
C2—C3	1.376 (4)	C16—H16	0.92 (3)
C3—C4	1.390 (4)	C17—C18	1.386 (4)
C3—H3	0.97 (3)	C17—H17	0.99 (3)
C4—C5	1.375 (4)	C18—H18	0.97 (3)

N1—Mn1—N4	70.63 (9)	N4—C6—H6	112.6 (19)
N1—Mn1—Cl2	143.46 (7)	C5—C6—H6	124.3 (19)
N4—Mn1—Cl2	105.24 (7)	N3—C7—N2	124.8 (3)
N1—Mn1—Cl1	105.99 (7)	N3—C7—C8	115.2 (3)
N4—Mn1—Cl1	102.96 (7)	N2—C7—C8	119.9 (3)
Cl2—Mn1—Cl1	110.21 (4)	N5—C8—C9	122.9 (3)
N1—Mn1—N6	70.16 (8)	N5—C8—C7	118.0 (3)
N4—Mn1—N6	137.01 (8)	C9—C8—C7	119.1 (3)
Cl2—Mn1—N6	95.92 (7)	C10—C9—C8	118.8 (3)
Cl1—Mn1—N6	104.10 (6)	C10—C9—H9	120.6 (19)
C13—N1—C1	115.8 (2)	C8—C9—H9	120.5 (19)
C13—N1—Mn1	122.03 (19)	C11—C10—C9	119.2 (3)
C1—N1—Mn1	122.03 (18)	C11—C10—H10	120 (2)
C1—N2—C7	114.3 (2)	C9—C10—H10	121 (2)
C13—N3—C7	115.1 (2)	C10—C11—C12	118.4 (3)
C6—N4—C2	117.1 (3)	C10—C11—H11	121 (2)
C6—N4—Mn1	125.9 (2)	C12—C11—H11	121 (2)
C2—N4—Mn1	116.75 (19)	N5—C12—C11	124.2 (3)
C12—N5—C8	116.5 (3)	N5—C12—H12	114.1 (19)
C18—N6—C14	117.4 (3)	C11—C12—H12	121.6 (19)
C18—N6—Mn1	125.8 (2)	N1—C13—N3	124.9 (3)
C14—N6—Mn1	116.04 (18)	N1—C13—C14	115.6 (3)
N2—C1—N1	124.7 (3)	N3—C13—C14	119.5 (3)
N2—C1—C2	120.8 (3)	N6—C14—C15	123.6 (3)
N1—C1—C2	114.5 (3)	N6—C14—C13	114.3 (2)
N4—C2—C3	123.1 (3)	C15—C14—C13	122.0 (3)
N4—C2—C1	114.8 (2)	C16—C15—C14	117.9 (3)
C3—C2—C1	122.1 (3)	C16—C15—H15	123 (2)
C2—C3—C4	118.8 (3)	C14—C15—H15	119 (2)
C2—C3—H3	115.7 (19)	C15—C16—C17	119.6 (3)
C4—C3—H3	125.4 (19)	C15—C16—H16	125 (2)
C5—C4—C3	118.5 (3)	C17—C16—H16	115 (2)
C5—C4—H4	119.9 (19)	C18—C17—C16	118.5 (3)
C3—C4—H4	121.6 (19)	C18—C17—H17	120.9 (18)
C4—C5—C6	119.4 (3)	C16—C17—H17	120.6 (18)
C4—C5—H5	123.1 (18)	N6—C18—C17	122.8 (3)
C6—C5—H5	117.6 (18)	N6—C18—H18	114.8 (17)
N4—C6—C5	123.1 (3)	C17—C18—H18	122.2 (17)

N4—Mn1—N1—C13	173.6 (2)	C3—C4—C5—C6	−0.7 (5)
Cl2—Mn1—N1—C13	84.0 (3)	C2—N4—C6—C5	0.2 (5)
Cl1—Mn1—N1—C13	−88.0 (2)	Mn1—N4—C6—C5	−173.1 (2)
N6—Mn1—N1—C13	11.6 (2)	C4—C5—C6—N4	0.4 (5)
N4—Mn1—N1—C1	−10.8 (2)	C13—N3—C7—N2	5.2 (4)
Cl2—Mn1—N1—C1	−100.4 (2)	C13—N3—C7—C8	−177.1 (3)
Cl1—Mn1—N1—C1	87.7 (2)	C1—N2—C7—N3	−5.6 (4)
N6—Mn1—N1—C1	−172.8 (2)	C1—N2—C7—C8	176.8 (3)
N1—Mn1—N4—C6	−177.8 (3)	C12—N5—C8—C9	0.7 (4)
Cl2—Mn1—N4—C6	−35.9 (3)	C12—N5—C8—C7	179.2 (3)
Cl1—Mn1—N4—C6	79.6 (3)	N3—C7—C8—N5	−175.0 (3)
N6—Mn1—N4—C6	−152.6 (2)	N2—C7—C8—N5	2.8 (4)
N1—Mn1—N4—C2	8.9 (2)	N3—C7—C8—C9	3.5 (4)
Cl2—Mn1—N4—C2	150.78 (19)	N2—C7—C8—C9	−178.7 (3)
Cl1—Mn1—N4—C2	−93.8 (2)	N5—C8—C9—C10	−0.8 (5)
N6—Mn1—N4—C2	34.1 (3)	C7—C8—C9—C10	−179.2 (3)
N1—Mn1—N6—C18	179.1 (3)	C8—C9—C10—C11	0.1 (5)
N4—Mn1—N6—C18	153.8 (2)	C9—C10—C11—C12	0.5 (5)
Cl2—Mn1—N6—C18	33.9 (2)	C8—N5—C12—C11	−0.1 (5)
Cl1—Mn1—N6—C18	−78.7 (3)	C10—C11—C12—N5	−0.6 (5)
N1—Mn1—N6—C14	−11.4 (2)	C1—N1—C13—N3	−5.2 (4)
N4—Mn1—N6—C14	−36.7 (3)	Mn1—N1—C13—N3	170.7 (2)
Cl2—Mn1—N6—C14	−156.7 (2)	C1—N1—C13—C14	173.8 (2)
Cl1—Mn1—N6—C14	90.8 (2)	Mn1—N1—C13—C14	−10.3 (3)
C7—N2—C1—N1	0.3 (4)	C7—N3—C13—N1	0.6 (4)
C7—N2—C1—C2	178.0 (3)	C7—N3—C13—C14	−178.4 (2)
C13—N1—C1—N2	4.7 (4)	C18—N6—C14—C15	0.2 (4)
Mn1—N1—C1—N2	−171.1 (2)	Mn1—N6—C14—C15	−170.2 (2)
C13—N1—C1—C2	−173.1 (3)	C18—N6—C14—C13	−179.2 (3)
Mn1—N1—C1—C2	11.0 (3)	Mn1—N6—C14—C13	10.4 (3)
C6—N4—C2—C3	−0.6 (4)	N1—C13—C14—N6	−0.9 (4)
Mn1—N4—C2—C3	173.4 (2)	N3—C13—C14—N6	178.1 (3)
C6—N4—C2—C1	179.4 (3)	N1—C13—C14—C15	179.7 (3)
Mn1—N4—C2—C1	−6.6 (3)	N3—C13—C14—C15	−1.3 (4)
N2—C1—C2—N4	179.9 (3)	N6—C14—C15—C16	2.1 (5)
N1—C1—C2—N4	−2.2 (4)	C13—C14—C15—C16	−178.6 (3)
N2—C1—C2—C3	−0.1 (4)	C14—C15—C16—C17	−2.1 (5)
N1—C1—C2—C3	177.8 (3)	C15—C16—C17—C18	0.0 (5)
N4—C2—C3—C4	0.3 (5)	C14—N6—C18—C17	−2.5 (5)
C1—C2—C3—C4	−179.7 (3)	Mn1—N6—C18—C17	166.8 (2)
C2—C3—C4—C5	0.4 (5)	C16—C17—C18—N6	2.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.91 (3)	2.76 (3)	3.589 (3)	151 (3)
C15—H15···Cl1ⁱⁱ	0.92 (3)	2.81 (3)	3.633 (4)	151 (2)
C3—H3···N2	0.97 (3)	2.52 (3)	2.896 (4)	103 (2)
C9—H9···N3	0.92 (3)	2.41 (3)	2.735 (4)	101 (2)
C15—H15···N3	0.92 (3)	2.57 (3)	2.869 (4)	100 (2)

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

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₈H₁₂N₆)]
M_r	438.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	10.8799 (9), 19.5524 (16), 8.6446 (7)
β (°)	101.051 (2)
V (Å³)	1804.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.29 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.826, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13299, 4450, 2653
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.01
No. of reflections	4450
No. of parameters	292
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.56

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

Selected geometric parameters (Å, º) top

Mn1—N1	2.189 (2)	Mn1—Cl1	2.3470 (10)
Mn1—N4	2.318 (2)	Mn1—Cl2	2.3400 (10)
Mn1—N6	2.348 (2)

N1—Mn1—N4	70.63 (9)	N1—Mn1—N6	70.16 (8)
Cl2—Mn1—Cl1	110.21 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.91 (3)	2.76 (3)	3.589 (3)	151 (3)
C15—H15···Cl1ⁱⁱ	0.92 (3)	2.81 (3)	3.633 (4)	151 (2)
C3—H3···N2	0.97 (3)	2.52 (3)	2.896 (4)	103 (2)
C9—H9···N3	0.92 (3)	2.41 (3)	2.735 (4)	101 (2)
C15—H15···N3	0.92 (3)	2.57 (3)	2.869 (4)	100 (2)

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

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 (grant No. 2010–0029626).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ha, K. (2010). Acta Cryst. E66, m262. 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

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