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Acta Cryst. (2007). E63, m3036    [ doi:10.1107/S1600536807055262 ]

Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dichloridomanganese(II) methanol disolvate

S. Jin and D. Wang

Abstract top

In the title compound, [MnCl2(C10H11N3)2]·2CH3OH, both naphthyridine ligands coordinate to the MnII ion via two N atoms in a bidentate chelating mode. The MnII centre is furthermore coordinated by two Cl ligands to form an octahedral geometry. In addition, there are two methanol molecules in the asymmetric unit. The crystal packing is stabilized by O-H...Cl, N-H...O and N-H...Cl hydrogen bonds.

Comment top

Molecular structures and chemical properties of transition metal complexes of 1,8-naphthyridine (napy) and its derivatives have received much attention, because the ligands can link to metals with several coordination modes such as monodentate, chelating bidentate, and dinuclear bridging binding fashion (Gavrilova & Bosnich, 2004). 5,7-dimethyl-1,8-naphthyridin-2-amine are potentially tridentate ligands and are capable of linking two to four metal atoms together to form metal aggregates having metal–metal interactions (Oskui et al., 1999; Mintert & Sheldrick, 1995a,b; Oskui & Sheldrick, 1999). The coordination chemistry of 5,7-dimethyl-1,8-naphthyridine-2-amine (L) has not been well studied before although a Mn(II) complex (Mn(L)2Cl2) (Bayer, 1979) was once described in a US patent. As an extension of our work (Jin et al., 2007), the title complex (Mn(L)2(Cl)2)·2(CH3OH) is reported here.

The complex was obtained as colorless crystals by reacting of manganese chloride tetrahydrate and L in methanol. The compound is air stable and light insensitive. The complex does not dissolve in water and common organic solvent. The molecular structure of the compound is shown in Fig. 1. Both of the two L coordinate to the metal with two N atoms in a bidentate chelating fashion. Two chloride anions coordinate to the Mn ion to complete its octahedral geometry. The amine group of 5,7-dimethyl-1,8-naphthyridin-2-amine does not show any bonding interaction with the Mn atoms. The Mn—N bond distances range from 2.231 (3) to 2.453 (3) Å. The Mn—Cl bond distances are 2.4166 (14) and 2.4699 (12) Å. The two naphthyridine rings are almost perpendicular to each other.

Related literature top

For related literature, see: Bayer (1979); Gavrilova & Bosnich (2004); Jin et al. (2007); Mintert & Sheldrick (1995a,b); Oskui et al. (1999); Oskui & Sheldrick (1999).

Experimental top

All reagents and solvents were used as obtained without further purification. The CHN elemental analyses were performed on a Perkin–Elmer elemental analyzer.

To an methanol solution of manganese chloride tetrahydrate (40 mg, 0.2 mmol) was added L (34.8 mg, 0.2 mmol) in 10 ml of methanol. The solution was stirred for a few minutes, then the solution was filtered. After standing the solution at room temperature for several days, colorless block crystals were isolated. Yield: 32.2 mg, 60%. Anal. Calcd. for C22H30Cl2MnN6O2: C, 49.22; H, 5.59; N, 15.66. Found: C, 49.17; H, 5.50; N, 15.62.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with O—H = 0.82 Å, N—H = 0.90 Å and C—H = 0.96 Å and U(H) set to 1.2Ueq(C,N,O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Three dimensional network structure connected via pi-pi interaction and hydrogen bonds.
Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dichloridomanganese(II) methanol disolvate top
Crystal data top
[MnCl2(C10H11N3)2]·2CH3OHZ = 2
Mr = 536.36F000 = 558
Triclinic, P1Dx = 1.354 Mg m−3
a = 9.637 (3) ÅMo Kα radiation
λ = 0.71073 Å
b = 10.649 (3) ÅCell parameters from 1874 reflections
c = 14.442 (4) Åθ = 2.4–23.2º
α = 79.178 (4)ºµ = 0.73 mm−1
β = 78.343 (4)ºT = 298 (2) K
γ = 65.894 (4)ºBlock, colourless
V = 1315.7 (7) Å30.41 × 0.22 × 0.17 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		4597 independent reflections
Radiation source: fine-focus sealed tube2867 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→11
Tmin = 0.753, Tmax = 0.885k = −12→11
6933 measured reflectionsl = −17→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4067P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4597 reflectionsΔρmax = 0.31 e Å−3
298 parametersΔρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[MnCl2(C10H11N3)2]·2CH3OHγ = 65.894 (4)º
Mr = 536.36V = 1315.7 (7) Å3
Triclinic, P1Z = 2
a = 9.637 (3) ÅMo Kα
b = 10.649 (3) ŵ = 0.73 mm−1
c = 14.442 (4) ÅT = 298 (2) K
α = 79.178 (4)º0.41 × 0.22 × 0.17 mm
β = 78.343 (4)º
Data collection top
Siemens SMART CCD area-detector
diffractometer		4597 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2867 reflections with I > 2σ(I)
Tmin = 0.753, Tmax = 0.885Rint = 0.020
6933 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047298 parameters
wR(F2) = 0.125H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å−3
4597 reflectionsΔρmin = −0.24 e Å−3
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 > 2sigma(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
xyzUiso*/Ueq
Mn10.03600 (6)0.77674 (5)0.25965 (4)0.04575 (19)
Cl10.05456 (13)0.98490 (10)0.29881 (7)0.0636 (3)
Cl2−0.24018 (12)0.85917 (13)0.27296 (7)0.0760 (4)
N10.2973 (3)0.7055 (3)0.1725 (2)0.0449 (7)
N20.0861 (3)0.7875 (3)0.10128 (19)0.0449 (7)
N3−0.1387 (4)0.8679 (4)0.0390 (2)0.0736 (10)
H3A−0.18790.87410.09580.088*
H3B−0.18800.8911−0.00900.088*
N40.0720 (3)0.5423 (3)0.29246 (19)0.0434 (7)
N50.1309 (3)0.6444 (3)0.39243 (19)0.0440 (7)
N60.1863 (4)0.7605 (3)0.4883 (2)0.0711 (10)
H6A0.15320.83480.44970.085*
H6B0.22060.76200.53850.085*
O10.2760 (4)0.7735 (3)0.6695 (2)0.0863 (10)
H10.20540.84660.68220.130*
O20.7131 (4)0.9445 (4)0.8698 (2)0.0924 (10)
H20.76550.97400.82660.139*
C10.2407 (4)0.7379 (3)0.0889 (2)0.0436 (8)
C20.0140 (5)0.8224 (4)0.0253 (3)0.0544 (10)
C30.0983 (5)0.8106 (4)−0.0680 (3)0.0621 (11)
H30.04700.8367−0.12090.075*
C40.2517 (5)0.7617 (4)−0.0791 (3)0.0625 (11)
H40.30630.7539−0.14010.075*
C50.3329 (5)0.7213 (4)0.0003 (2)0.0497 (9)
C60.4929 (5)0.6667 (4)−0.0013 (3)0.0596 (11)
C70.5471 (5)0.6343 (4)0.0835 (3)0.0644 (11)
H70.65260.59810.08430.077*
C80.4486 (5)0.6537 (4)0.1696 (3)0.0554 (10)
C90.6011 (5)0.6424 (5)−0.0936 (3)0.0815 (14)
H9A0.60510.7289−0.12510.122*
H9B0.56500.6034−0.13390.122*
H9C0.70180.5796−0.08060.122*
C100.5090 (5)0.6191 (5)0.2626 (3)0.0782 (13)
H10A0.42750.66250.31110.117*
H10B0.58960.65220.25720.117*
H10C0.54850.52050.27940.117*
C110.1292 (4)0.5249 (3)0.3733 (2)0.0414 (8)
C120.1846 (4)0.6429 (4)0.4704 (3)0.0502 (9)
C130.2383 (4)0.5185 (4)0.5337 (3)0.0564 (10)
H130.27500.51890.58840.068*
C140.2361 (4)0.4015 (4)0.5147 (3)0.0568 (10)
H140.27130.32110.55650.068*
C150.1809 (4)0.3981 (4)0.4314 (2)0.0485 (9)
C160.1720 (5)0.2840 (4)0.4025 (3)0.0572 (10)
C170.1094 (5)0.3053 (4)0.3206 (3)0.0591 (11)
H170.10080.23130.30020.071*
C180.0586 (4)0.4350 (4)0.2675 (3)0.0517 (9)
C190.2261 (6)0.1429 (4)0.4589 (3)0.0798 (14)
H19A0.31530.12890.48590.120*
H19B0.25150.07320.41780.120*
H19C0.14610.13670.50910.120*
C20−0.0165 (5)0.4602 (5)0.1806 (3)0.0722 (12)
H20A−0.10790.44080.19790.108*
H20B0.05320.40080.13460.108*
H20C−0.04280.55520.15360.108*
C210.4129 (6)0.7950 (6)0.6425 (4)0.1003 (17)
H21A0.41270.86160.67910.150*
H21B0.42200.82900.57600.150*
H21C0.49800.70910.65370.150*
C220.5636 (6)1.0004 (5)0.8526 (5)0.118 (2)
H22A0.50280.96400.90240.177*
H22B0.55880.97710.79260.177*
H22C0.52471.09930.85070.177*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0506 (4)0.0454 (3)0.0389 (3)−0.0156 (3)−0.0108 (2)−0.0012 (2)
Cl10.0821 (8)0.0473 (6)0.0639 (6)−0.0256 (5)−0.0129 (6)−0.0079 (5)
Cl20.0492 (6)0.1008 (9)0.0613 (7)−0.0161 (6)−0.0116 (5)0.0040 (6)
N10.0466 (19)0.0405 (17)0.0457 (17)−0.0131 (15)−0.0121 (14)−0.0028 (13)
N20.0467 (19)0.0462 (18)0.0384 (16)−0.0137 (15)−0.0107 (14)−0.0013 (13)
N30.057 (2)0.104 (3)0.051 (2)−0.018 (2)−0.0218 (18)−0.0040 (19)
N40.0463 (18)0.0482 (18)0.0388 (16)−0.0209 (15)−0.0084 (14)−0.0033 (13)
N50.0527 (19)0.0428 (17)0.0413 (16)−0.0222 (15)−0.0124 (14)−0.0005 (13)
N60.109 (3)0.069 (2)0.055 (2)−0.045 (2)−0.034 (2)−0.0028 (17)
O10.065 (2)0.101 (2)0.080 (2)−0.0100 (19)−0.0094 (17)−0.0327 (18)
O20.073 (2)0.132 (3)0.074 (2)−0.046 (2)−0.0337 (18)0.0206 (19)
C10.049 (2)0.0359 (19)0.045 (2)−0.0161 (17)−0.0083 (18)−0.0013 (16)
C20.057 (3)0.050 (2)0.054 (3)−0.018 (2)−0.015 (2)−0.0012 (18)
C30.078 (3)0.068 (3)0.039 (2)−0.026 (2)−0.016 (2)−0.0006 (19)
C40.081 (3)0.063 (3)0.041 (2)−0.031 (2)0.007 (2)−0.0085 (19)
C50.060 (3)0.044 (2)0.044 (2)−0.0191 (19)−0.007 (2)−0.0045 (17)
C60.061 (3)0.047 (2)0.067 (3)−0.023 (2)0.004 (2)−0.008 (2)
C70.043 (2)0.066 (3)0.077 (3)−0.017 (2)−0.002 (2)−0.010 (2)
C80.050 (3)0.050 (2)0.067 (3)−0.019 (2)−0.017 (2)−0.0002 (19)
C90.070 (3)0.084 (3)0.081 (3)−0.032 (3)0.024 (3)−0.021 (3)
C100.059 (3)0.092 (3)0.083 (3)−0.026 (3)−0.032 (2)0.007 (3)
C110.040 (2)0.044 (2)0.040 (2)−0.0179 (17)−0.0021 (16)−0.0032 (16)
C120.056 (2)0.056 (2)0.044 (2)−0.026 (2)−0.0086 (18)−0.0068 (18)
C130.061 (3)0.068 (3)0.040 (2)−0.024 (2)−0.0177 (19)0.0034 (19)
C140.056 (3)0.053 (2)0.048 (2)−0.014 (2)−0.0062 (19)0.0090 (18)
C150.050 (2)0.043 (2)0.045 (2)−0.0143 (18)−0.0051 (18)0.0002 (17)
C160.057 (3)0.047 (2)0.061 (3)−0.019 (2)0.002 (2)−0.0045 (19)
C170.061 (3)0.048 (2)0.071 (3)−0.025 (2)0.003 (2)−0.018 (2)
C180.048 (2)0.058 (3)0.054 (2)−0.024 (2)−0.0019 (18)−0.0147 (19)
C190.098 (4)0.047 (3)0.088 (3)−0.026 (3)−0.012 (3)0.002 (2)
C200.069 (3)0.091 (3)0.072 (3)−0.037 (3)−0.015 (2)−0.025 (2)
C210.083 (4)0.107 (4)0.108 (4)−0.027 (3)−0.017 (3)−0.023 (3)
C220.090 (4)0.080 (4)0.190 (7)−0.035 (3)−0.058 (4)0.014 (4)
Geometric parameters (Å, °) top
Mn1—N22.231 (3)C7—C81.395 (5)
Mn1—N52.267 (3)C7—H70.9300
Mn1—N42.344 (3)C8—C101.495 (5)
Mn1—Cl22.4166 (14)C9—H9A0.9600
Mn1—N12.453 (3)C9—H9B0.9600
Mn1—Cl12.4699 (12)C9—H9C0.9600
N1—C81.327 (5)C10—H10A0.9600
N1—C11.353 (4)C10—H10B0.9600
N2—C21.331 (4)C10—H10C0.9600
N2—C11.347 (4)C11—C151.403 (5)
N3—C21.332 (5)C12—C131.426 (5)
N3—H3A0.8600C13—C141.333 (5)
N3—H3B0.8600C13—H130.9300
N4—C181.322 (4)C14—C151.422 (5)
N4—C111.341 (4)C14—H140.9300
N5—C121.326 (4)C15—C161.396 (5)
N5—C111.359 (4)C16—C171.374 (5)
N6—C121.332 (4)C16—C191.505 (5)
N6—H6A0.8600C17—C181.392 (5)
N6—H6B0.8600C17—H170.9300
O1—C211.396 (5)C18—C201.501 (5)
O1—H10.8200C19—H19A0.9600
O2—C221.371 (5)C19—H19B0.9600
O2—H20.8200C19—H19C0.9600
C1—C51.398 (5)C20—H20A0.9600
C2—C31.424 (5)C20—H20B0.9600
C3—C41.338 (5)C20—H20C0.9600
C3—H30.9300C21—H21A0.9600
C4—C51.420 (5)C21—H21B0.9600
C4—H40.9300C21—H21C0.9600
C5—C61.405 (5)C22—H22A0.9600
C6—C71.359 (6)C22—H22B0.9600
C6—C91.509 (5)C22—H22C0.9600
N2—Mn1—N5140.98 (10)C6—C9—H9B109.5
N2—Mn1—N497.82 (10)H9A—C9—H9B109.5
N5—Mn1—N458.08 (9)C6—C9—H9C109.5
N2—Mn1—Cl297.46 (8)H9A—C9—H9C109.5
N5—Mn1—Cl2113.38 (8)H9B—C9—H9C109.5
N4—Mn1—Cl294.45 (8)C8—C10—H10A109.5
N2—Mn1—N156.89 (10)C8—C10—H10B109.5
N5—Mn1—N189.71 (10)H10A—C10—H10B109.5
N4—Mn1—N188.28 (9)C8—C10—H10C109.5
Cl2—Mn1—N1154.31 (8)H10A—C10—H10C109.5
N2—Mn1—Cl1105.51 (8)H10B—C10—H10C109.5
N5—Mn1—Cl193.36 (7)N4—C11—N5112.1 (3)
N4—Mn1—Cl1151.42 (8)N4—C11—C15123.8 (3)
Cl2—Mn1—Cl198.59 (5)N5—C11—C15124.1 (3)
N1—Mn1—Cl190.77 (7)N5—C12—N6118.4 (3)
C8—N1—C1117.8 (3)N5—C12—C13120.6 (3)
C8—N1—Mn1151.8 (3)N6—C12—C13121.0 (3)
C1—N1—Mn190.4 (2)C14—C13—C12120.3 (3)
C2—N2—C1119.0 (3)C14—C13—H13119.9
C2—N2—Mn1140.4 (3)C12—C13—H13119.9
C1—N2—Mn1100.6 (2)C13—C14—C15120.9 (3)
C2—N3—H3A120.0C13—C14—H14119.5
C2—N3—H3B120.0C15—C14—H14119.5
H3A—N3—H3B120.0C16—C15—C11117.6 (3)
C18—N4—C11118.2 (3)C16—C15—C14127.2 (3)
C18—N4—Mn1148.4 (2)C11—C15—C14115.2 (3)
C11—N4—Mn193.44 (19)C17—C16—C15117.4 (3)
C12—N5—C11118.8 (3)C17—C16—C19120.7 (4)
C12—N5—Mn1144.8 (2)C15—C16—C19121.8 (4)
C11—N5—Mn196.3 (2)C16—C17—C18121.6 (3)
C12—N6—H6A120.0C16—C17—H17119.2
C12—N6—H6B120.0C18—C17—H17119.2
H6A—N6—H6B120.0N4—C18—C17121.3 (4)
C21—O1—H1109.5N4—C18—C20116.9 (3)
C22—O2—H2109.5C17—C18—C20121.7 (4)
N2—C1—N1112.1 (3)C16—C19—H19A109.5
N2—C1—C5124.4 (3)C16—C19—H19B109.5
N1—C1—C5123.5 (3)H19A—C19—H19B109.5
N2—C2—N3118.2 (4)C16—C19—H19C109.5
N2—C2—C3120.7 (4)H19A—C19—H19C109.5
N3—C2—C3121.1 (4)H19B—C19—H19C109.5
C4—C3—C2119.5 (4)C18—C20—H20A109.5
C4—C3—H3120.2C18—C20—H20B109.5
C2—C3—H3120.2H20A—C20—H20B109.5
C3—C4—C5121.5 (4)C18—C20—H20C109.5
C3—C4—H4119.3H20A—C20—H20C109.5
C5—C4—H4119.3H20B—C20—H20C109.5
C1—C5—C6117.9 (3)O1—C21—H21A109.5
C1—C5—C4115.0 (4)O1—C21—H21B109.5
C6—C5—C4127.1 (4)H21A—C21—H21B109.5
C7—C6—C5117.5 (4)O1—C21—H21C109.5
C7—C6—C9121.1 (4)H21A—C21—H21C109.5
C5—C6—C9121.4 (4)H21B—C21—H21C109.5
C6—C7—C8121.7 (4)O2—C22—H22A109.5
C6—C7—H7119.1O2—C22—H22B109.5
C8—C7—H7119.1H22A—C22—H22B109.5
N1—C8—C7121.6 (4)O2—C22—H22C109.5
N1—C8—C10117.0 (4)H22A—C22—H22C109.5
C7—C8—C10121.5 (4)H22B—C22—H22C109.5
C6—C9—H9A109.5
N2—Mn1—N1—C8−177.8 (5)N3—C2—C3—C4−178.5 (4)
N5—Mn1—N1—C8−19.2 (5)C2—C3—C4—C5−0.1 (6)
N4—Mn1—N1—C8−77.3 (5)N2—C1—C5—C6−179.3 (3)
Cl2—Mn1—N1—C8−174.0 (4)N1—C1—C5—C60.7 (5)
Cl1—Mn1—N1—C874.1 (5)N2—C1—C5—C40.2 (5)
N2—Mn1—N1—C1−0.35 (18)N1—C1—C5—C4−179.8 (3)
N5—Mn1—N1—C1158.21 (19)C3—C4—C5—C1−0.5 (5)
N4—Mn1—N1—C1100.13 (19)C3—C4—C5—C6178.9 (4)
Cl2—Mn1—N1—C13.4 (3)C1—C5—C6—C7−0.3 (5)
Cl1—Mn1—N1—C1−108.44 (18)C4—C5—C6—C7−179.7 (4)
N5—Mn1—N2—C2143.0 (3)C1—C5—C6—C9178.6 (3)
N4—Mn1—N2—C295.7 (4)C4—C5—C6—C9−0.8 (6)
Cl2—Mn1—N2—C20.2 (4)C5—C6—C7—C80.2 (6)
N1—Mn1—N2—C2178.5 (4)C9—C6—C7—C8−178.8 (4)
Cl1—Mn1—N2—C2−100.9 (4)C1—N1—C8—C70.7 (5)
N5—Mn1—N2—C1−35.1 (3)Mn1—N1—C8—C7177.8 (3)
N4—Mn1—N2—C1−82.4 (2)C1—N1—C8—C10179.8 (3)
Cl2—Mn1—N2—C1−177.99 (19)Mn1—N1—C8—C10−3.1 (7)
N1—Mn1—N2—C10.36 (18)C6—C7—C8—N1−0.3 (6)
Cl1—Mn1—N2—C180.9 (2)C6—C7—C8—C10−179.4 (4)
N2—Mn1—N4—C18−35.6 (5)C18—N4—C11—N5−177.5 (3)
N5—Mn1—N4—C18177.5 (5)Mn1—N4—C11—N51.7 (3)
Cl2—Mn1—N4—C1862.6 (5)C18—N4—C11—C152.4 (5)
N1—Mn1—N4—C18−91.8 (5)Mn1—N4—C11—C15−178.4 (3)
Cl1—Mn1—N4—C18179.8 (4)C12—N5—C11—N4180.0 (3)
N2—Mn1—N4—C11145.8 (2)Mn1—N5—C11—N4−1.8 (3)
N5—Mn1—N4—C11−1.12 (19)C12—N5—C11—C150.1 (5)
Cl2—Mn1—N4—C11−115.98 (19)Mn1—N5—C11—C15178.4 (3)
N1—Mn1—N4—C1189.6 (2)C11—N5—C12—N6179.7 (3)
Cl1—Mn1—N4—C111.2 (3)Mn1—N5—C12—N62.7 (7)
N2—Mn1—N5—C12119.4 (4)C11—N5—C12—C13−0.6 (5)
N4—Mn1—N5—C12178.5 (5)Mn1—N5—C12—C13−177.6 (3)
Cl2—Mn1—N5—C12−101.3 (4)N5—C12—C13—C140.5 (6)
N1—Mn1—N5—C1290.3 (4)N6—C12—C13—C14−179.8 (4)
Cl1—Mn1—N5—C12−0.5 (4)C12—C13—C14—C150.1 (6)
N2—Mn1—N5—C11−58.0 (3)N4—C11—C15—C160.2 (5)
N4—Mn1—N5—C111.11 (18)N5—C11—C15—C16180.0 (3)
Cl2—Mn1—N5—C1181.3 (2)N4—C11—C15—C14−179.4 (3)
N1—Mn1—N5—C11−87.1 (2)N5—C11—C15—C140.4 (5)
Cl1—Mn1—N5—C11−177.80 (19)C13—C14—C15—C16180.0 (4)
C2—N2—C1—N1−179.2 (3)C13—C14—C15—C11−0.5 (5)
Mn1—N2—C1—N1−0.6 (3)C11—C15—C16—C17−1.7 (5)
C2—N2—C1—C50.8 (5)C14—C15—C16—C17177.8 (4)
Mn1—N2—C1—C5179.5 (3)C11—C15—C16—C19179.2 (3)
C8—N1—C1—N2179.1 (3)C14—C15—C16—C19−1.3 (6)
Mn1—N1—C1—N20.5 (3)C15—C16—C17—C180.9 (6)
C8—N1—C1—C5−0.9 (5)C19—C16—C17—C18179.9 (4)
Mn1—N1—C1—C5−179.5 (3)C11—N4—C18—C17−3.3 (5)
C1—N2—C2—N3178.2 (3)Mn1—N4—C18—C17178.3 (3)
Mn1—N2—C2—N30.3 (6)C11—N4—C18—C20175.6 (3)
C1—N2—C2—C3−1.4 (5)Mn1—N4—C18—C20−2.8 (7)
Mn1—N2—C2—C3−179.4 (3)C16—C17—C18—N41.7 (6)
N2—C2—C3—C41.1 (6)C16—C17—C18—C20−177.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Cl1i0.822.353.162 (3)169
O1—H1···Cl1ii0.822.413.183 (3)158
N6—H6B···O10.862.102.960 (4)173
N6—H6A···Cl10.862.553.359 (4)158
N3—H3B···O2iii0.862.042.895 (4)175
N3—H3A···Cl20.862.493.318 (4)161
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y, z−1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Cl1i0.822.353.162 (3)169
O1—H1···Cl1ii0.822.413.183 (3)158
N6—H6B···O10.862.102.960 (4)173
N6—H6A···Cl10.862.553.359 (4)158
N3—H3B···O2iii0.862.042.895 (4)175
N3—H3A···Cl20.862.493.318 (4)161
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y, z−1.
Acknowledgements top

The authors thank Zhejiang Forestry University Science Foundation for financial support.

references
References top

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