{N,N′-Bis[1-(2-pyrid­yl)ethyl­idene]propane-1,2-diamine-κ4N,N′,N′′,N′′′}bis­(thio­cyanato-κN)manganese(II)

Wang, F.-M.

doi:10.1107/S1600536810021549

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m777

doi:10.1107/S1600536810021549

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{N,N′-Bis[1-(2-pyridyl)ethylidene]propane-1,2-diamine-κ⁴N,N′,N′′,N′′′}bis(thiocyanato-κN)manganese(II)

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 6 June 2010; accepted 6 June 2010; online 16 June 2010)

In the title compound, [Mn(NCS)₂(C₁₇H₂₀N₄)], the Mn^II atom is six-coordinated by the N,N′,N′′,N′′′-tetradentate Schiff base ligand and by two trans-N atoms from two thiocyanate anions, forming a distorted octahedral geometry. The dihedral angle between the aromatic rings of the Schiff base is 9.5 (3)°.

Related literature

For another complex containing 1,2-bis(2′-pyridylmethyleneamino)propane, see: Ouyang et al. (2002 ). For related manganese(II) complexes with Schiff bases, see: Louloudi et al. (1999 ); Sra et al. (2000 ); Karmakar et al. (2005 ); Deoghoria et al. (2005 ). For the synthesis of the Schiff base, see: Gourbatsis et al. (1990 ).

Experimental

Crystal data

[Mn(NCS)₂(C₁₇H₂₀N₄)]
M_r = 451.47
Triclinic, $[P \overline 1]$
a = 8.647 (3) Å
b = 9.135 (2) Å
c = 14.608 (3) Å
α = 84.701 (3)°
β = 79.407 (3)°
γ = 70.509 (3)°
V = 1068.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 298 K
0.33 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.771, T_max = 0.789
11100 measured reflections
4608 independent reflections
2211 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.224
S = 0.99
4608 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N5	2.127 (6)
Mn1—N6	2.149 (6)
Mn1—N2	2.258 (5)
Mn1—N3	2.260 (4)
Mn1—N4	2.334 (4)
Mn1—N1	2.346 (4)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021549/hb5486sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021549/hb5486Isup2.hkl

checkCIF report

Comment top

Metal complexes with Schiff bases have been known since 1840 but only one complex derived from 1,2-bis(2'-pyridylmethyleneamino)propane has been reported (Ouyang et al., 2002). In this paper, the title new manganese(II) complex is reported.

In the title complex, Fig. 1, the Mn^II atom is six-coordinated by four N atoms of the Schiff base ligand 1,2-bis(2'-pyridylmethyleneamino)propane, and by two N atoms from two thiocyanate ligands, forming a distorted octahedral geometry. The coordinate bond lengths (Table 1) are comparable with those observed in other similar manganese(II) complexes with Schiff bases (Louloudi et al., 1999; Sra et al., 2000; Karmakar et al., 2005; Deoghoria et al., 2005).

Related literature top

For another complex containing 1,2-bis(2'-pyridylmethyleneamino)propane, see: Ouyang et al. (2002). For related manganese(II) complexes with Schiff bases, see: Louloudi et al. (1999); Sra et al. (2000); Karmakar et al. (2005); Deoghoria et al. (2005). For the synthesis of the Schiff base, see: Gourbatsis et al. (1990).

Experimental top

The Schiff base ligand 1,2-bis(2'-pyridylmethyleneamino)propane was synthesized according to the literature method (Gourbatsis et al., 1990). To a stirred methanol solution of the Schiff base ligand (1.0 mmol, 0.280 g) was added a methanol solution of manganese acetate (1.0 mmol, 0.245 g) and ammonium thiocyanate (1.0 mmol, 0.076 g). The mixture was boiled under reflux for 2 h, then cooled to room temperature. Brown blocks of (I) were formed after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 30% probability level.

{N,N'-Bis[1-(2-pyridyl)ethylidene]propane-1,2-diamine- κ⁴N,N',N'',N'''}bis(thiocyanato- κN)manganese(II) top

Crystal data top

[Mn(NCS)₂(C₁₇H₂₀N₄)]	Z = 2
M_r = 451.47	F(000) = 466
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.647 (3) Å	Cell parameters from 1307 reflections
b = 9.135 (2) Å	θ = 2.3–24.5°
c = 14.608 (3) Å	µ = 0.83 mm⁻¹
α = 84.701 (3)°	T = 298 K
β = 79.407 (3)°	Block, brown
γ = 70.509 (3)°	0.33 × 0.30 × 0.30 mm
V = 1068.6 (5) Å³

Data collection top

Bruker SMART CCD diffractometer	4608 independent reflections
Radiation source: fine-focus sealed tube	2211 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scan	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.771, T_max = 0.789	k = −11→11
11100 measured reflections	l = −18→18

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.224	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1044P)²] where P = (F_o² + 2F_c²)/3
4608 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Mn(NCS)₂(C₁₇H₂₀N₄)]	γ = 70.509 (3)°
M_r = 451.47	V = 1068.6 (5) Å³
Triclinic, P1	Z = 2
a = 8.647 (3) Å	Mo Kα radiation
b = 9.135 (2) Å	µ = 0.83 mm⁻¹
c = 14.608 (3) Å	T = 298 K
α = 84.701 (3)°	0.33 × 0.30 × 0.30 mm
β = 79.407 (3)°

Data collection top

Bruker SMART CCD diffractometer	4608 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2211 reflections with I > 2σ(I)
T_min = 0.771, T_max = 0.789	R_int = 0.078
11100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.224	H-atom parameters constrained
S = 0.99	Δρ_max = 0.68 e Å⁻³
4608 reflections	Δρ_min = −0.34 e Å⁻³
256 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	1.02210 (10)	0.54382 (9)	0.27241 (5)	0.0601 (3)
N1	1.2061 (6)	0.6565 (5)	0.3134 (3)	0.0644 (12)
N2	1.0220 (6)	0.7580 (5)	0.1819 (3)	0.0673 (12)
N3	0.8157 (6)	0.5912 (5)	0.1875 (3)	0.0701 (13)
N4	0.9013 (5)	0.3471 (5)	0.3008 (3)	0.0665 (12)
N5	0.8737 (7)	0.6394 (7)	0.3994 (4)	0.0906 (17)
N6	1.2282 (6)	0.3744 (6)	0.1940 (4)	0.0772 (15)
S1	0.6757 (2)	0.8093 (2)	0.54416 (16)	0.1097 (7)
S2	1.4735 (2)	0.1575 (2)	0.08162 (12)	0.0855 (5)
C1	1.2937 (8)	0.6060 (8)	0.3826 (5)	0.089 (2)
H1	1.2883	0.5148	0.4151	0.107*
C2	1.3917 (9)	0.6811 (8)	0.4088 (5)	0.096 (2)
H2	1.4508	0.6422	0.4578	0.116*
C3	1.3997 (8)	0.8144 (8)	0.3608 (5)	0.088 (2)
H3	1.4654	0.8677	0.3765	0.106*
C4	1.3109 (7)	0.8693 (6)	0.2897 (5)	0.0750 (17)
H4	1.3155	0.9601	0.2565	0.090*
C5	1.2135 (6)	0.7880 (6)	0.2674 (4)	0.0574 (13)
C6	1.1124 (7)	0.8394 (7)	0.1905 (4)	0.0631 (14)
C7	1.1270 (9)	0.9785 (7)	0.1307 (5)	0.095 (2)
H7A	1.2372	0.9548	0.0956	0.142*
H7B	1.1054	1.0646	0.1696	0.142*
H7C	1.0477	1.0050	0.0888	0.142*
C8	0.9234 (8)	0.7889 (8)	0.1062 (4)	0.087 (2)
H8	0.8913	0.8996	0.0880	0.104*
C9	1.0322 (10)	0.6917 (9)	0.0230 (5)	0.106 (2)
H9A	1.1312	0.7198	0.0042	0.159*
H9B	0.9712	0.7114	−0.0281	0.159*
H9C	1.0619	0.5833	0.0409	0.159*
C10	0.7743 (8)	0.7434 (8)	0.1372 (5)	0.098 (2)
H10A	0.7250	0.7379	0.0837	0.118*
H10B	0.6935	0.8213	0.1779	0.118*
C11	0.7315 (7)	0.4988 (6)	0.1900 (4)	0.0617 (14)
C12	0.5892 (7)	0.5241 (7)	0.1393 (5)	0.0843 (19)
H12A	0.5809	0.6123	0.0970	0.126*
H12B	0.4880	0.5428	0.1833	0.126*
H12C	0.6072	0.4335	0.1050	0.126*
C13	0.7763 (6)	0.3606 (6)	0.2541 (4)	0.0613 (14)
C14	0.6956 (7)	0.2485 (8)	0.2671 (5)	0.0826 (18)
H14	0.6105	0.2573	0.2340	0.099*
C15	0.7432 (8)	0.1242 (8)	0.3297 (5)	0.094 (2)
H15	0.6899	0.0495	0.3389	0.112*
C16	0.8672 (9)	0.1124 (8)	0.3771 (5)	0.094 (2)
H16	0.9006	0.0303	0.4195	0.112*
C17	0.9429 (8)	0.2251 (7)	0.3610 (4)	0.0808 (18)
H17	1.0283	0.2165	0.3937	0.097*
C18	0.7938 (7)	0.7096 (6)	0.4577 (4)	0.0589 (14)
C19	1.3320 (7)	0.2828 (7)	0.1471 (4)	0.0631 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0670 (6)	0.0649 (6)	0.0607 (5)	−0.0367 (5)	−0.0173 (4)	0.0090 (4)
N1	0.082 (3)	0.060 (3)	0.064 (3)	−0.036 (2)	−0.024 (2)	0.011 (2)
N2	0.078 (3)	0.075 (3)	0.066 (3)	−0.041 (3)	−0.030 (2)	0.012 (2)
N3	0.075 (3)	0.072 (3)	0.077 (3)	−0.039 (3)	−0.026 (3)	0.017 (3)
N4	0.063 (3)	0.077 (3)	0.071 (3)	−0.036 (2)	−0.018 (2)	0.009 (3)
N5	0.089 (4)	0.110 (5)	0.082 (4)	−0.051 (4)	−0.001 (3)	−0.006 (3)
N6	0.079 (4)	0.077 (4)	0.086 (4)	−0.040 (3)	−0.016 (3)	0.003 (3)
S1	0.0955 (14)	0.1071 (16)	0.1234 (16)	−0.0214 (12)	−0.0135 (12)	−0.0410 (13)
S2	0.0850 (12)	0.0822 (12)	0.0928 (12)	−0.0285 (10)	−0.0153 (9)	−0.0139 (9)
C1	0.116 (5)	0.088 (5)	0.091 (5)	−0.060 (4)	−0.049 (4)	0.026 (4)
C2	0.114 (5)	0.099 (5)	0.102 (5)	−0.051 (5)	−0.063 (4)	0.019 (4)
C3	0.096 (5)	0.078 (5)	0.115 (5)	−0.047 (4)	−0.047 (4)	0.001 (4)
C4	0.080 (4)	0.052 (3)	0.103 (5)	−0.029 (3)	−0.030 (4)	0.003 (3)
C5	0.055 (3)	0.060 (3)	0.062 (3)	−0.025 (3)	−0.010 (3)	−0.006 (3)
C6	0.065 (3)	0.067 (4)	0.064 (3)	−0.030 (3)	−0.015 (3)	0.008 (3)
C7	0.121 (6)	0.080 (5)	0.103 (5)	−0.061 (4)	−0.037 (4)	0.039 (4)
C8	0.113 (5)	0.080 (5)	0.085 (4)	−0.049 (4)	−0.042 (4)	0.027 (4)
C9	0.143 (7)	0.102 (6)	0.083 (5)	−0.051 (5)	−0.026 (5)	0.003 (4)
C10	0.108 (5)	0.110 (6)	0.110 (5)	−0.070 (5)	−0.060 (4)	0.042 (4)
C11	0.057 (3)	0.059 (3)	0.075 (4)	−0.026 (3)	−0.011 (3)	−0.005 (3)
C12	0.065 (4)	0.088 (5)	0.112 (5)	−0.032 (3)	−0.037 (4)	0.006 (4)
C13	0.056 (3)	0.064 (4)	0.069 (3)	−0.032 (3)	0.002 (3)	−0.004 (3)
C14	0.067 (4)	0.086 (5)	0.113 (5)	−0.046 (4)	−0.021 (4)	0.000 (4)
C15	0.094 (5)	0.090 (5)	0.113 (6)	−0.059 (4)	−0.015 (4)	0.022 (4)
C16	0.099 (5)	0.089 (5)	0.106 (5)	−0.054 (4)	−0.022 (4)	0.034 (4)
C17	0.087 (4)	0.086 (5)	0.088 (4)	−0.047 (4)	−0.034 (4)	0.022 (4)
C18	0.057 (4)	0.052 (4)	0.075 (4)	−0.026 (3)	−0.022 (3)	0.013 (3)
C19	0.063 (4)	0.061 (4)	0.075 (4)	−0.030 (3)	−0.024 (3)	0.013 (3)

Geometric parameters (Å, º) top

Mn1—N5	2.127 (6)	C5—C6	1.495 (7)
Mn1—N6	2.149 (6)	C6—C7	1.501 (8)
Mn1—N2	2.258 (5)	C7—H7A	0.9600
Mn1—N3	2.260 (4)	C7—H7B	0.9600
Mn1—N4	2.334 (4)	C7—H7C	0.9600
Mn1—N1	2.346 (4)	C8—C10	1.465 (8)
N1—C1	1.331 (7)	C8—C9	1.540 (9)
N1—C5	1.336 (6)	C8—H8	0.9800
N2—C6	1.274 (6)	C9—H9A	0.9600
N2—C8	1.470 (7)	C9—H9B	0.9600
N3—C11	1.281 (6)	C9—H9C	0.9600
N3—C10	1.476 (7)	C10—H10A	0.9700
N4—C17	1.345 (7)	C10—H10B	0.9700
N4—C13	1.348 (6)	C11—C13	1.486 (8)
N5—C18	1.097 (7)	C11—C12	1.493 (7)
N6—C19	1.164 (7)	C12—H12A	0.9600
S1—C18	1.608 (7)	C12—H12B	0.9600
S2—C19	1.600 (7)	C12—H12C	0.9600
C1—C2	1.376 (8)	C13—C14	1.402 (7)
C1—H1	0.9300	C14—C15	1.389 (8)
C2—C3	1.364 (9)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.351 (8)
C3—C4	1.364 (8)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.376 (8)
C4—C5	1.389 (7)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300

N5—Mn1—N6	152.6 (2)	H7A—C7—H7B	109.5
N5—Mn1—N2	102.5 (2)	C6—C7—H7C	109.5
N6—Mn1—N2	99.53 (18)	H7A—C7—H7C	109.5
N5—Mn1—N3	98.1 (2)	H7B—C7—H7C	109.5
N6—Mn1—N3	103.71 (18)	C10—C8—N2	109.6 (5)
N2—Mn1—N3	73.15 (16)	C10—C8—C9	109.9 (6)
N5—Mn1—N4	86.78 (19)	N2—C8—C9	107.8 (5)
N6—Mn1—N4	85.41 (17)	C10—C8—H8	109.8
N2—Mn1—N4	142.80 (16)	N2—C8—H8	109.8
N3—Mn1—N4	69.88 (16)	C9—C8—H8	109.8
N5—Mn1—N1	82.92 (18)	C8—C9—H9A	109.5
N6—Mn1—N1	89.82 (17)	C8—C9—H9B	109.5
N2—Mn1—N1	69.50 (15)	H9A—C9—H9B	109.5
N3—Mn1—N1	141.88 (17)	C8—C9—H9C	109.5
N4—Mn1—N1	147.69 (16)	H9A—C9—H9C	109.5
C1—N1—C5	117.9 (5)	H9B—C9—H9C	109.5
C1—N1—Mn1	125.2 (4)	C8—C10—N3	110.8 (5)
C5—N1—Mn1	116.7 (3)	C8—C10—H10A	109.5
C6—N2—C8	121.8 (5)	N3—C10—H10A	109.5
C6—N2—Mn1	122.4 (4)	C8—C10—H10B	109.5
C8—N2—Mn1	115.5 (3)	N3—C10—H10B	109.5
C11—N3—C10	122.6 (5)	H10A—C10—H10B	108.1
C11—N3—Mn1	122.1 (4)	N3—C11—C13	115.4 (5)
C10—N3—Mn1	114.9 (3)	N3—C11—C12	125.6 (5)
C17—N4—C13	117.9 (5)	C13—C11—C12	118.9 (5)
C17—N4—Mn1	125.7 (4)	C11—C12—H12A	109.5
C13—N4—Mn1	116.3 (3)	C11—C12—H12B	109.5
C18—N5—Mn1	169.2 (6)	H12A—C12—H12B	109.5
C19—N6—Mn1	174.9 (5)	C11—C12—H12C	109.5
N1—C1—C2	123.6 (6)	H12A—C12—H12C	109.5
N1—C1—H1	118.2	H12B—C12—H12C	109.5
C2—C1—H1	118.2	N4—C13—C14	120.4 (5)
C3—C2—C1	118.0 (6)	N4—C13—C11	116.3 (5)
C3—C2—H2	121.0	C14—C13—C11	123.3 (5)
C1—C2—H2	121.0	C15—C14—C13	119.7 (6)
C2—C3—C4	119.7 (6)	C15—C14—H14	120.2
C2—C3—H3	120.1	C13—C14—H14	120.2
C4—C3—H3	120.1	C16—C15—C14	119.6 (6)
C3—C4—C5	119.2 (6)	C16—C15—H15	120.2
C3—C4—H4	120.4	C14—C15—H15	120.2
C5—C4—H4	120.4	C15—C16—C17	118.2 (6)
N1—C5—C4	121.6 (5)	C15—C16—H16	120.9
N1—C5—C6	115.6 (4)	C17—C16—H16	120.9
C4—C5—C6	122.8 (5)	N4—C17—C16	124.2 (6)
N2—C6—C5	115.6 (5)	N4—C17—H17	117.9
N2—C6—C7	126.2 (5)	C16—C17—H17	117.9
C5—C6—C7	118.2 (5)	N5—C18—S1	178.7 (6)
C6—C7—H7A	109.5	N6—C19—S2	179.4 (6)
C6—C7—H7B	109.5

Experimental details

Crystal data
Chemical formula	[Mn(NCS)₂(C₁₇H₂₀N₄)]
M_r	451.47
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.647 (3), 9.135 (2), 14.608 (3)
α, β, γ (°)	84.701 (3), 79.407 (3), 70.509 (3)
V (Å³)	1068.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.33 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.771, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	11100, 4608, 2211
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.224, 0.99
No. of reflections	4608
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.34

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—N5	2.127 (6)	Mn1—N3	2.260 (4)
Mn1—N6	2.149 (6)	Mn1—N4	2.334 (4)
Mn1—N2	2.258 (5)	Mn1—N1	2.346 (4)

Acknowledgements

This work was supported by Dezhou University, People's Republic of China.

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