[2,6-Bis(6-methyl­quinolin-2-yl)pyridine-κ3N,N′,N′′]dichloridomanganese(II)

Li, X.-P.; Zhao, J.-S.; Ng, S.W.

doi:10.1107/S1600536810037037

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1298

doi:10.1107/S1600536810037037

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[2,6-Bis(6-methylquinolin-2-yl)pyridine-κ³N,N′,N′′]dichloridomanganese(II)

Xiao-Ping Li,^a Jian-She Zhao ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Shaanxi Key Laboratory for Physico-Inorganic Chemistry, Northwest University, Xi'an 710069, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 September 2010; accepted 16 September 2010; online 25 September 2010)

In the molecule of the title compound, [MnCl₂(C₂₅H₁₉N₃)], the three N atoms span the axial–equatorial–axial sites of the trigonal-bipyramidal coordination polyhedron; the geometry of the Mn^II atom is 34% distorted from trigonal-bipyramidal (towards square-pyramidal along the Berry pseudorotation pathway). One of the Cl atoms is disordered over two positions in a 0.82 (3):0.18 (3) ratio. Weak intermolecular C—H⋯Cl hydrogen bonding occurs in the crystal structure.

Related literature

For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965 ). For a related structure, see: Li et al. (2010 ).

Experimental

Crystal data

[MnCl₂(C₂₅H₁₉N₃)]
M_r = 487.27
Triclinic, $[P \overline 1]$
a = 9.6763 (8) Å
b = 10.3721 (9) Å
c = 10.5757 (9) Å
α = 95.099 (1)°
β = 97.499 (1)°
γ = 95.411 (1)°
V = 1042.13 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.772, T_max = 0.956
10000 measured reflections
4760 independent reflections
3704 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.151
S = 1.03
4760 reflections
292 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N1	2.305 (3)
Mn1—N2	2.186 (3)
Mn1—N3	2.332 (3)
Mn1—Cl1	2.3802 (17)
Mn1—Cl2	2.3375 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl2ⁱ	0.95	2.64	3.486 (5)	149
C17—H17⋯Cl1ⁱⁱ	0.95	2.72	3.500 (9)	140
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037037/xu5031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037037/xu5031Isup2.hkl

checkCIF report

Comment top

A recent study reported the chromium(III) chloride adduct of 2,6-bis(p-bromphenylimino)pyridine; the N-heterocycle chelates to the metal atom in a terdentate manner (Li et al., 2010). Bis[2'-(6-methylquinolinyl)]pyridine has a similar set of donor sites capable of binding in this manner, as demonstrated in the present manganese dichloride adduct (Scheme I, Fig. 1). In the molecule of MnCl₂(C₂₅H₁₉N₃), the three N atoms span the axial–equatorial-axial sites of the trigonal bipyramidal coordination polyhedron; the geometry of Fe is 34% distorted from the trigonal bipyramid along the Berry pseudorotation pathway. Intermolecular weak C—H···Cl hydrogen bonding occurs in the crystal structure (Table 2).

Related literature top

For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965). For a related structure, see: Li et al. (2010).

Experimental top

The ligand was synthesized by using a literature procedure (Buu-Hoi et al., 1965).

Bis[2'-(6-methylquinolinyl)]pyridine (0.018 g, 0.05 mmol), and manganese chloride tetrahydrate (0.01 g, 0.05 mmol) along with five drops of 1 M hydrochloric acid were dissolved in ethanol (10 ml). The mixture was heated in a Teflon-lined, stainless-steel Parr bomb at 363 K for 120 h. The bomb was cooled at 5 K per hour. Deep orange crystals were isolated.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of MnCl₂(C₂₅H₁₉N₃) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

[2,6-Bis(6-methylquinolin-2-yl)pyridine- κ³N,N',N'']dichloridomanganese(II) top

Crystal data top

[MnCl₂(C₂₅H₁₉N₃)]	Z = 2
M_r = 487.27	F(000) = 498
Triclinic, P1	D_x = 1.553 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6763 (8) Å	Cell parameters from 2981 reflections
b = 10.3721 (9) Å	θ = 2.7–28.1°
c = 10.5757 (9) Å	µ = 0.91 mm⁻¹
α = 95.099 (1)°	T = 100 K
β = 97.499 (1)°	Prism, orange
γ = 95.411 (1)°	0.30 × 0.10 × 0.05 mm
V = 1042.13 (15) Å³

Data collection top

Bruker SMART APEX diffractometer	4760 independent reflections
Radiation source: fine-focus sealed tube	3704 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.772, T_max = 0.956	k = −13→13
10000 measured reflections	l = −13→13

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0695P)² + 1.8956P] where P = (F_o² + 2F_c²)/3
4760 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.61 e Å⁻³
7 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

[MnCl₂(C₂₅H₁₉N₃)]	γ = 95.411 (1)°
M_r = 487.27	V = 1042.13 (15) Å³
Triclinic, P1	Z = 2
a = 9.6763 (8) Å	Mo Kα radiation
b = 10.3721 (9) Å	µ = 0.91 mm⁻¹
c = 10.5757 (9) Å	T = 100 K
α = 95.099 (1)°	0.30 × 0.10 × 0.05 mm
β = 97.499 (1)°

Data collection top

Bruker SMART APEX diffractometer	4760 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3704 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.956	R_int = 0.031
10000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	7 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.61 e Å⁻³
4760 reflections	Δρ_min = −0.62 e Å⁻³
292 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.34023 (5)	0.80899 (5)	0.22288 (5)	0.02281 (16)
Cl1	0.1607 (7)	0.7350 (2)	0.3414 (7)	0.0280 (8)	0.82 (3)
Cl1'	0.202 (4)	0.7316 (11)	0.378 (3)	0.033 (4)	0.18 (3)
Cl2	0.26785 (12)	0.84219 (10)	0.00968 (9)	0.0408 (3)
N1	0.4349 (3)	0.6152 (3)	0.1893 (3)	0.0246 (6)
N2	0.5637 (3)	0.8443 (3)	0.2966 (3)	0.0218 (6)
N3	0.3883 (3)	1.0248 (3)	0.3127 (3)	0.0233 (6)
C1	0.3623 (4)	0.5007 (3)	0.1294 (3)	0.0238 (7)
C2	0.2180 (4)	0.4980 (4)	0.0882 (4)	0.0315 (8)
H2	0.1724	0.5744	0.1012	0.038*
C3	0.1431 (4)	0.3852 (3)	0.0292 (4)	0.0307 (8)
H3	0.0455	0.3848	0.0020	0.037*
C4	0.2061 (4)	0.2698 (3)	0.0075 (3)	0.0258 (7)
C5	0.3468 (4)	0.2715 (3)	0.0468 (3)	0.0268 (7)
H5	0.3910	0.1945	0.0326	0.032*
C6	0.4273 (4)	0.3862 (3)	0.1081 (3)	0.0268 (7)
C7	0.1162 (4)	0.1491 (3)	−0.0556 (4)	0.0300 (8)
H7A	0.1753	0.0788	−0.0692	0.045*
H7B	0.0676	0.1671	−0.1384	0.045*
H7C	0.0470	0.1226	−0.0004	0.045*
C8	0.5703 (5)	0.3949 (4)	0.1535 (4)	0.0449 (10)
H8	0.6196	0.3205	0.1431	0.054*
C9	0.6412 (5)	0.5111 (5)	0.2137 (4)	0.0452 (10)
H9	0.7382	0.5156	0.2454	0.054*
C10	0.5714 (3)	0.6197 (3)	0.2276 (3)	0.0218 (7)
C11	0.6441 (3)	0.7459 (3)	0.2886 (3)	0.0234 (7)
C12	0.7870 (3)	0.7643 (4)	0.3346 (3)	0.0250 (7)
H12	0.8430	0.6941	0.3287	0.030*
C13	0.8453 (4)	0.8864 (4)	0.3890 (3)	0.0294 (8)
H13	0.9426	0.9013	0.4201	0.035*
C14	0.7620 (4)	0.9875 (3)	0.3982 (3)	0.0268 (7)
H14	0.8007	1.0719	0.4358	0.032*
C15	0.6196 (3)	0.9620 (3)	0.3508 (3)	0.0224 (7)
C16	0.5199 (4)	1.0619 (3)	0.3558 (3)	0.0257 (7)
C17	0.5635 (5)	1.1919 (5)	0.4056 (5)	0.0507 (11)
H17	0.6597	1.2182	0.4356	0.061*
C18	0.4660 (5)	1.2819 (5)	0.4109 (5)	0.0514 (12)
H18	0.4963	1.3696	0.4442	0.062*
C19	0.3264 (4)	1.2453 (3)	0.3686 (3)	0.0262 (7)
C20	0.2218 (4)	1.3312 (3)	0.3691 (3)	0.0281 (8)
H20	0.2470	1.4196	0.4025	0.034*
C21	0.0836 (4)	1.2892 (3)	0.3220 (3)	0.0288 (8)
C22	0.0497 (4)	1.1579 (3)	0.2710 (3)	0.0273 (7)
H22	−0.0448	1.1280	0.2370	0.033*
C23	0.1494 (4)	1.0724 (3)	0.2691 (3)	0.0266 (7)
H23	0.1230	0.9844	0.2349	0.032*
C24	0.2906 (4)	1.1140 (3)	0.3175 (3)	0.0252 (7)
C25	−0.0286 (4)	1.3793 (4)	0.3212 (4)	0.0363 (9)
H25A	0.0144	1.4697	0.3304	0.055*
H25B	−0.0816	1.3654	0.3926	0.055*
H25C	−0.0920	1.3618	0.2400	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0177 (3)	0.0206 (3)	0.0285 (3)	0.00071 (19)	0.0000 (2)	−0.00009 (19)
Cl1	0.0207 (13)	0.0246 (6)	0.0377 (16)	−0.0016 (7)	0.0049 (13)	0.0008 (7)
Cl1'	0.026 (7)	0.031 (3)	0.040 (6)	−0.003 (3)	0.008 (6)	−0.003 (3)
Cl2	0.0500 (6)	0.0386 (5)	0.0323 (5)	0.0163 (4)	−0.0063 (4)	0.0018 (4)
N1	0.0245 (15)	0.0239 (14)	0.0248 (14)	0.0002 (11)	0.0016 (12)	0.0044 (11)
N2	0.0199 (14)	0.0219 (14)	0.0222 (13)	−0.0013 (11)	0.0007 (11)	0.0013 (10)
N3	0.0243 (15)	0.0230 (14)	0.0230 (14)	0.0021 (11)	0.0056 (11)	0.0013 (11)
C1	0.0210 (17)	0.0246 (16)	0.0240 (16)	−0.0048 (13)	−0.0002 (13)	0.0051 (13)
C2	0.0276 (19)	0.0251 (18)	0.040 (2)	0.0040 (14)	0.0006 (16)	0.0013 (15)
C3	0.0240 (18)	0.0284 (18)	0.036 (2)	−0.0020 (14)	−0.0037 (15)	0.0017 (15)
C4	0.0324 (19)	0.0213 (16)	0.0234 (16)	−0.0006 (14)	0.0044 (14)	0.0035 (13)
C5	0.0303 (19)	0.0253 (17)	0.0259 (17)	0.0047 (14)	0.0050 (14)	0.0062 (13)
C6	0.0251 (18)	0.0309 (18)	0.0246 (17)	0.0016 (14)	0.0022 (14)	0.0077 (14)
C7	0.033 (2)	0.0240 (17)	0.0318 (19)	−0.0015 (15)	0.0034 (15)	0.0036 (14)
C8	0.045 (3)	0.039 (2)	0.052 (3)	0.0141 (19)	0.009 (2)	0.0015 (19)
C9	0.032 (2)	0.054 (3)	0.048 (2)	0.0101 (19)	0.0015 (19)	0.000 (2)
C10	0.0163 (15)	0.0232 (16)	0.0257 (16)	−0.0003 (12)	0.0036 (13)	0.0032 (13)
C11	0.0203 (16)	0.0299 (18)	0.0200 (15)	0.0047 (13)	0.0012 (13)	0.0035 (13)
C12	0.0174 (16)	0.0330 (18)	0.0236 (16)	0.0010 (13)	0.0008 (13)	0.0017 (14)
C13	0.0174 (17)	0.045 (2)	0.0247 (17)	−0.0012 (15)	0.0012 (13)	0.0034 (15)
C14	0.0236 (18)	0.0297 (18)	0.0241 (16)	−0.0066 (14)	0.0020 (13)	−0.0022 (14)
C15	0.0206 (16)	0.0256 (17)	0.0198 (15)	−0.0034 (13)	0.0030 (12)	0.0019 (12)
C16	0.0261 (18)	0.0268 (17)	0.0225 (16)	−0.0050 (14)	0.0030 (13)	0.0017 (13)
C17	0.047 (3)	0.055 (3)	0.047 (3)	0.000 (2)	0.002 (2)	0.003 (2)
C18	0.060 (3)	0.041 (2)	0.051 (3)	−0.001 (2)	0.007 (2)	0.002 (2)
C19	0.0278 (18)	0.0258 (17)	0.0253 (17)	0.0009 (14)	0.0050 (14)	0.0042 (13)
C20	0.034 (2)	0.0226 (17)	0.0284 (18)	0.0020 (14)	0.0062 (15)	0.0050 (13)
C21	0.033 (2)	0.0279 (18)	0.0280 (17)	0.0068 (15)	0.0084 (15)	0.0079 (14)
C22	0.0265 (18)	0.0276 (18)	0.0280 (17)	0.0024 (14)	0.0039 (14)	0.0045 (14)
C23	0.0272 (18)	0.0220 (16)	0.0294 (17)	0.0005 (14)	0.0030 (14)	−0.0002 (13)
C24	0.0285 (18)	0.0251 (17)	0.0231 (16)	0.0018 (14)	0.0064 (14)	0.0053 (13)
C25	0.034 (2)	0.0282 (19)	0.048 (2)	0.0066 (16)	0.0070 (18)	0.0060 (17)

Geometric parameters (Å, º) top

Mn1—N1	2.305 (3)	C9—H9	0.9500
Mn1—N2	2.186 (3)	C10—C11	1.477 (5)
Mn1—N3	2.332 (3)	C11—C12	1.393 (5)
Mn1—Cl1	2.3802 (17)	C12—C13	1.381 (5)
Mn1—Cl1'	2.388 (7)	C12—H12	0.9500
Mn1—Cl2	2.3375 (11)	C13—C14	1.385 (5)
N1—C10	1.325 (4)	C13—H13	0.9500
N1—C1	1.378 (4)	C14—C15	1.395 (5)
N2—C15	1.335 (4)	C14—H14	0.9500
N2—C11	1.344 (4)	C15—C16	1.483 (5)
N3—C16	1.305 (4)	C16—C17	1.408 (6)
N3—C24	1.387 (5)	C17—C18	1.391 (7)
C1—C2	1.405 (5)	C17—H17	0.9500
C1—C6	1.410 (5)	C18—C19	1.373 (6)
C2—C3	1.370 (5)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.410 (5)
C3—C4	1.408 (5)	C19—C24	1.413 (5)
C3—H3	0.9500	C20—C21	1.380 (5)
C4—C5	1.369 (5)	C20—H20	0.9500
C4—C7	1.505 (5)	C21—C22	1.411 (5)
C5—C6	1.414 (5)	C21—C25	1.498 (5)
C5—H5	0.9500	C22—C23	1.372 (5)
C6—C8	1.396 (6)	C22—H22	0.9500
C7—H7A	0.9800	C23—C24	1.407 (5)
C7—H7B	0.9800	C23—H23	0.9500
C7—H7C	0.9800	C25—H25A	0.9800
C8—C9	1.386 (6)	C25—H25B	0.9800
C8—H8	0.9500	C25—H25C	0.9800
C9—C10	1.373 (6)

N2—Mn1—N1	72.62 (10)	C8—C9—H9	119.9
N2—Mn1—N3	71.80 (10)	N1—C10—C9	121.3 (3)
N1—Mn1—N3	144.34 (10)	N1—C10—C11	117.0 (3)
N2—Mn1—Cl2	118.47 (8)	C9—C10—C11	121.6 (3)
N1—Mn1—Cl2	99.09 (8)	N2—C11—C12	121.2 (3)
N3—Mn1—Cl2	99.72 (8)	N2—C11—C10	115.7 (3)
N2—Mn1—Cl1	125.3 (2)	C12—C11—C10	123.1 (3)
N1—Mn1—Cl1	98.25 (11)	C13—C12—C11	118.6 (3)
N3—Mn1—Cl1	100.18 (10)	C13—C12—H12	120.7
Cl2—Mn1—Cl1	116.2 (2)	C11—C12—H12	120.7
N2—Mn1—Cl1'	112.7 (11)	C12—C13—C14	120.1 (3)
N1—Mn1—Cl1'	93.8 (5)	C12—C13—H13	120.0
N3—Mn1—Cl1'	97.6 (3)	C14—C13—H13	120.0
Cl2—Mn1—Cl1'	128.8 (11)	C13—C14—C15	118.2 (3)
Cl1—Mn1—Cl1'	12.6 (9)	C13—C14—H14	120.9
C10—N1—C1	119.5 (3)	C15—C14—H14	120.9
C10—N1—Mn1	115.3 (2)	N2—C15—C14	121.6 (3)
C1—N1—Mn1	125.2 (2)	N2—C15—C16	115.2 (3)
C15—N2—C11	120.2 (3)	C14—C15—C16	123.2 (3)
C15—N2—Mn1	120.4 (2)	N3—C16—C17	120.5 (4)
C11—N2—Mn1	119.4 (2)	N3—C16—C15	117.4 (3)
C16—N3—C24	119.6 (3)	C17—C16—C15	122.1 (3)
C16—N3—Mn1	115.1 (2)	C18—C17—C16	120.2 (4)
C24—N3—Mn1	125.2 (2)	C18—C17—H17	119.9
N1—C1—C2	118.7 (3)	C16—C17—H17	119.9
N1—C1—C6	122.5 (3)	C19—C18—C17	120.6 (4)
C2—C1—C6	118.8 (3)	C19—C18—H18	119.7
C3—C2—C1	119.9 (3)	C17—C18—H18	119.7
C3—C2—H2	120.1	C18—C19—C20	123.9 (4)
C1—C2—H2	120.1	C18—C19—C24	116.1 (4)
C2—C3—C4	122.1 (3)	C20—C19—C24	120.0 (3)
C2—C3—H3	118.9	C21—C20—C19	121.2 (3)
C4—C3—H3	118.9	C21—C20—H20	119.4
C5—C4—C3	118.5 (3)	C19—C20—H20	119.4
C5—C4—C7	122.5 (3)	C20—C21—C22	118.1 (3)
C3—C4—C7	118.9 (3)	C20—C21—C25	121.9 (3)
C4—C5—C6	120.9 (3)	C22—C21—C25	120.0 (3)
C4—C5—H5	119.6	C23—C22—C21	121.8 (3)
C6—C5—H5	119.6	C23—C22—H22	119.1
C8—C6—C1	115.9 (3)	C21—C22—H22	119.1
C8—C6—C5	124.3 (4)	C22—C23—C24	120.5 (3)
C1—C6—C5	119.8 (3)	C22—C23—H23	119.8
C4—C7—H7A	109.5	C24—C23—H23	119.8
C4—C7—H7B	109.5	N3—C24—C23	118.7 (3)
H7A—C7—H7B	109.5	N3—C24—C19	122.9 (3)
C4—C7—H7C	109.5	C23—C24—C19	118.4 (3)
H7A—C7—H7C	109.5	C21—C25—H25A	109.5
H7B—C7—H7C	109.5	C21—C25—H25B	109.5
C9—C8—C6	120.6 (4)	H25A—C25—H25B	109.5
C9—C8—H8	119.7	C21—C25—H25C	109.5
C6—C8—H8	119.7	H25A—C25—H25C	109.5
C10—C9—C8	120.1 (4)	H25B—C25—H25C	109.5
C10—C9—H9	119.9

N2—Mn1—N1—C10	−0.7 (2)	C1—N1—C10—C11	178.6 (3)
N3—Mn1—N1—C10	−4.7 (3)	Mn1—N1—C10—C11	1.2 (4)
Cl2—Mn1—N1—C10	116.4 (2)	C8—C9—C10—N1	2.9 (6)
Cl1—Mn1—N1—C10	−125.2 (3)	C8—C9—C10—C11	−178.6 (4)
Cl1'—Mn1—N1—C10	−113.3 (10)	C15—N2—C11—C12	−0.8 (5)
N2—Mn1—N1—C1	−177.9 (3)	Mn1—N2—C11—C12	−179.9 (2)
N3—Mn1—N1—C1	178.1 (2)	C15—N2—C11—C10	179.6 (3)
Cl2—Mn1—N1—C1	−60.8 (3)	Mn1—N2—C11—C10	0.5 (4)
Cl1—Mn1—N1—C1	57.5 (3)	N1—C10—C11—N2	−1.2 (4)
Cl1'—Mn1—N1—C1	69.4 (10)	C9—C10—C11—N2	−179.8 (3)
N1—Mn1—N2—C15	−179.0 (3)	N1—C10—C11—C12	179.2 (3)
N3—Mn1—N2—C15	−1.5 (2)	C9—C10—C11—C12	0.6 (5)
Cl2—Mn1—N2—C15	89.9 (2)	N2—C11—C12—C13	−0.1 (5)
Cl1—Mn1—N2—C15	−91.2 (3)	C10—C11—C12—C13	179.4 (3)
Cl1'—Mn1—N2—C15	−92.3 (4)	C11—C12—C13—C14	0.7 (5)
N1—Mn1—N2—C11	0.1 (2)	C12—C13—C14—C15	−0.3 (5)
N3—Mn1—N2—C11	177.6 (3)	C11—N2—C15—C14	1.1 (5)
Cl2—Mn1—N2—C11	−91.0 (2)	Mn1—N2—C15—C14	−179.7 (2)
Cl1—Mn1—N2—C11	87.9 (3)	C11—N2—C15—C16	−179.1 (3)
Cl1'—Mn1—N2—C11	86.8 (4)	Mn1—N2—C15—C16	0.0 (4)
N2—Mn1—N3—C16	3.0 (2)	C13—C14—C15—N2	−0.6 (5)
N1—Mn1—N3—C16	6.9 (3)	C13—C14—C15—C16	179.7 (3)
Cl2—Mn1—N3—C16	−114.0 (2)	C24—N3—C16—C17	−0.8 (5)
Cl1—Mn1—N3—C16	127.0 (3)	Mn1—N3—C16—C17	176.4 (3)
Cl1'—Mn1—N3—C16	114.4 (11)	C24—N3—C16—C15	178.8 (3)
N2—Mn1—N3—C24	180.0 (3)	Mn1—N3—C16—C15	−4.0 (4)
N1—Mn1—N3—C24	−176.0 (2)	N2—C15—C16—N3	2.8 (4)
Cl2—Mn1—N3—C24	63.1 (3)	C14—C15—C16—N3	−177.4 (3)
Cl1—Mn1—N3—C24	−56.0 (3)	N2—C15—C16—C17	−177.6 (3)
Cl1'—Mn1—N3—C24	−68.5 (11)	C14—C15—C16—C17	2.2 (5)
C10—N1—C1—C2	−179.3 (3)	N3—C16—C17—C18	0.9 (6)
Mn1—N1—C1—C2	−2.2 (4)	C15—C16—C17—C18	−178.7 (4)
C10—N1—C1—C6	0.8 (5)	C16—C17—C18—C19	0.4 (7)
Mn1—N1—C1—C6	177.9 (2)	C17—C18—C19—C20	−179.0 (4)
N1—C1—C2—C3	−179.5 (3)	C17—C18—C19—C24	−1.6 (6)
C6—C1—C2—C3	0.3 (5)	C18—C19—C20—C21	178.2 (4)
C1—C2—C3—C4	−0.1 (6)	C24—C19—C20—C21	0.9 (5)
C2—C3—C4—C5	−0.2 (6)	C19—C20—C21—C22	−1.1 (5)
C2—C3—C4—C7	178.8 (3)	C19—C20—C21—C25	−179.6 (3)
C3—C4—C5—C6	0.2 (5)	C20—C21—C22—C23	1.0 (5)
C7—C4—C5—C6	−178.7 (3)	C25—C21—C22—C23	179.6 (3)
N1—C1—C6—C8	1.0 (5)	C21—C22—C23—C24	−0.7 (5)
C2—C1—C6—C8	−178.8 (4)	C16—N3—C24—C23	179.3 (3)
N1—C1—C6—C5	179.6 (3)	Mn1—N3—C24—C23	2.4 (4)
C2—C1—C6—C5	−0.3 (5)	C16—N3—C24—C19	−0.5 (5)
C4—C5—C6—C8	178.4 (4)	Mn1—N3—C24—C19	−177.4 (2)
C4—C5—C6—C1	0.0 (5)	C22—C23—C24—N3	−179.3 (3)
C1—C6—C8—C9	−0.9 (6)	C22—C23—C24—C19	0.4 (5)
C5—C6—C8—C9	−179.4 (4)	C18—C19—C24—N3	1.7 (5)
C6—C8—C9—C10	−0.9 (7)	C20—C19—C24—N3	179.2 (3)
C1—N1—C10—C9	−2.8 (5)	C18—C19—C24—C23	−178.1 (4)
Mn1—N1—C10—C9	179.8 (3)	C20—C19—C24—C23	−0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl2ⁱ	0.95	2.64	3.486 (5)	149
C17—H17···Cl1ⁱⁱ	0.95	2.72	3.500 (9)	140

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

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₂₅H₁₉N₃)]
M_r	487.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6763 (8), 10.3721 (9), 10.5757 (9)
α, β, γ (°)	95.099 (1), 97.499 (1), 95.411 (1)
V (Å³)	1042.13 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.772, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	10000, 4760, 3704
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.151, 1.03
No. of reflections	4760
No. of parameters	292
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.62

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Mn1—N1	2.305 (3)	Mn1—Cl1	2.3802 (17)
Mn1—N2	2.186 (3)	Mn1—Cl2	2.3375 (11)
Mn1—N3	2.332 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl2ⁱ	0.95	2.64	3.486 (5)	149
C17—H17···Cl1ⁱⁱ	0.95	2.72	3.500 (9)	140

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

Acknowledgements

We thank the Graduate Experimental Research Fund of Northwest University (project No. 09YSY22), the National Natural Science Foundation of China (No. 20971104) and the University of Malaya for supporting this study.

References

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