Bis-(thio-cyanato-κN)[tris(pyridin-2-yl-meth-yl)amine-κ(4) N]-iron(II).

In the title complex, [Fe(NCS)2(C18H18N4)], the Fe(II) cation is chelated by a tris-(2-pyridyl-meth-yl)amine ligand and coordin-ated by two thio-cyanate anions in a distorted N6 octa-hedral geometry. In the crystal, weak C-H⋯S hydrogen bonds and π-π stacking inter-actions between parallel pyridine rings of adjacent mol-ecules [centroid-centroid distance = 3.653 (3) Å] link the mol-ecules into a two-dimensional supra-molecular architecture. The structure contains voids of 124 (9) Å(3), which are free of solvent molecules.

Related literature

For the magnetic properties of metal complexes with tris­(2-pyridyl­meth­yl)amine and thio­cyanate ligands, see: Boldog et al. (2009 ▶); Li et al. (2010 ▶). For related complexes, see: Benhamou et al. (2008 ▶); Min et al. (2008 ▶); Phan et al. (2012 ▶); Wei et al. (2011 ▶).

Experimental

Crystal data

[Fe(NCS)2(C18H18N4)]

M = 462.37

Monoclinic,

a = 23.714 (5) Å

b = 11.827 (2) Å

c = 17.580 (3) Å

β = 112.87 (3)°

V = 4543.0 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 123 K

0.20 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn70 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.84, T max = 0.92

10256 measured reflections

4456 independent reflections

3275 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.203

S = 1.11

4456 reflections

283 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813034818/xu5762sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034818/xu5762Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Fe(NCS)2(C18H18N4)]	F(000) = 1904
Mr = 462.37	Dx = 1.352 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5300 reflections
a = 23.714 (5) Å	θ = 3.1–27.5°
b = 11.827 (2) Å	µ = 0.87 mm−1
c = 17.580 (3) Å	T = 123 K
β = 112.87 (3)°	Block, yellow
V = 4543.0 (18) Å3	0.20 × 0.20 × 0.10 mm
Z = 8

Rigaku Saturn70 diffractometer	4456 independent reflections
Radiation source: Rotating Anode	3275 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.059
Detector resolution: 28.5714 pixels mm-1	θmax = 26.0°, θmin = 3.1°
dtprofit.ref scans	h = −29→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −13→14
Tmin = 0.84, Tmax = 0.92	l = −21→15
10256 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0906P)2 + 9.7621P] where P = (Fo2 + 2Fc2)/3
4456 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.4648 (2)	0.4925 (4)	0.3477 (3)	0.0314 (12)
H1	0.4527	0.5481	0.3053	0.038*
C2	0.5264 (3)	0.4840 (6)	0.3995 (4)	0.0453 (16)
C3	0.5440 (3)	0.4028 (6)	0.4600 (4)	0.0500 (18)
H3	0.5858	0.3957	0.4960	0.060*
C4	0.5011 (3)	0.3321 (5)	0.4683 (4)	0.0442 (15)
H4	0.5126	0.2749	0.5095	0.053*
C5	0.4394 (2)	0.3459 (4)	0.4144 (3)	0.0291 (11)
C6	0.3910 (3)	0.2752 (5)	0.4272 (3)	0.0308 (12)
C7	0.3845 (3)	0.2760 (5)	0.1662 (4)	0.0365 (13)
C8	0.4054 (3)	0.1794 (5)	0.1395 (4)	0.0515 (18)
C9	0.3991 (3)	0.0772 (5)	0.1708 (4)	0.0537 (19)
H9	0.4129	0.0104	0.1534	0.064*
C10	0.3727 (3)	0.0710 (4)	0.2277 (4)	0.0394 (14)
H10	0.3684	0.0003	0.2507	0.047*
C11	0.3524 (2)	0.1698 (4)	0.2509 (3)	0.0269 (11)
C12	0.3195 (2)	0.1693 (4)	0.3090 (3)	0.0301 (12)
H12A	0.2750	0.1604	0.2770	0.036*
H12B	0.3337	0.1043	0.3473	0.036*
C13	0.3010 (2)	0.6046 (4)	0.3840 (3)	0.0268 (11)
H13	0.3135	0.6574	0.3528	0.032*
C14	0.2846 (3)	0.6447 (4)	0.4460 (4)	0.0334 (13)
C15	0.2664 (3)	0.5696 (4)	0.4917 (4)	0.0368 (13)
H15	0.2550	0.5950	0.5349	0.044*
C16	0.2654 (3)	0.4564 (5)	0.4731 (4)	0.0374 (14)
C17	0.2822 (2)	0.4211 (4)	0.4102 (3)	0.0239 (10)
C18	0.2812 (3)	0.2989 (4)	0.3860 (4)	0.0322 (12)
H18A	0.2862	0.2501	0.4340	0.039*
H18B	0.2412	0.2809	0.3414	0.039*
C19	0.3519 (2)	0.6301 (4)	0.1751 (3)	0.0280 (11)
C20	0.1843 (2)	0.3861 (4)	0.1455 (3)	0.0283 (11)
Fe1	0.32597 (3)	0.41694 (5)	0.26973 (4)	0.0221 (2)
H2	0.550 (2)	0.542 (4)	0.396 (3)	0.026*
H7	0.391 (2)	0.349 (5)	0.147 (3)	0.026*
H8	0.416 (2)	0.182 (4)	0.092 (3)	0.026*
H14	0.287 (2)	0.726 (4)	0.459 (3)	0.026*
H16	0.248 (2)	0.408 (4)	0.495 (3)	0.026*
H6A	0.405 (2)	0.203 (5)	0.442 (3)	0.026*
H6B	0.382 (2)	0.298 (4)	0.469 (3)	0.026*
N1	0.42170 (18)	0.4244 (3)	0.3555 (3)	0.0259 (9)
N2	0.35696 (18)	0.2708 (3)	0.2191 (3)	0.0256 (9)
N3	0.30029 (17)	0.4938 (3)	0.3656 (2)	0.0201 (8)
N4	0.33090 (18)	0.2760 (3)	0.3573 (3)	0.0240 (9)
N5	0.3355 (2)	0.5542 (4)	0.2041 (3)	0.0376 (11)
N6	0.23443 (19)	0.3841 (3)	0.1954 (3)	0.0303 (10)
S1	0.37451 (7)	0.73656 (12)	0.13592 (10)	0.0415 (4)
S2	0.11437 (7)	0.39138 (13)	0.07738 (11)	0.0517 (5)

	U11	U22	U33	U12	U13	U23
C1	0.029 (3)	0.035 (3)	0.030 (3)	−0.009 (2)	0.012 (2)	−0.006 (2)
C2	0.026 (3)	0.060 (4)	0.048 (4)	−0.013 (3)	0.013 (3)	−0.030 (3)
C3	0.023 (3)	0.081 (5)	0.042 (4)	0.005 (3)	0.008 (3)	−0.028 (4)
C4	0.032 (3)	0.060 (4)	0.034 (3)	0.021 (3)	0.007 (3)	−0.008 (3)
C5	0.029 (3)	0.032 (3)	0.023 (3)	0.010 (2)	0.007 (2)	−0.004 (2)
C6	0.040 (3)	0.028 (3)	0.022 (3)	0.010 (2)	0.010 (2)	0.007 (2)
C7	0.049 (3)	0.031 (3)	0.033 (3)	0.000 (2)	0.021 (3)	0.002 (2)
C8	0.084 (5)	0.038 (3)	0.054 (4)	0.001 (3)	0.050 (4)	−0.003 (3)
C9	0.090 (5)	0.030 (3)	0.063 (5)	0.015 (3)	0.053 (4)	0.003 (3)
C10	0.060 (4)	0.025 (3)	0.044 (4)	0.002 (3)	0.033 (3)	−0.003 (2)
C11	0.034 (3)	0.021 (2)	0.026 (3)	0.001 (2)	0.011 (2)	−0.002 (2)
C12	0.043 (3)	0.020 (2)	0.032 (3)	−0.002 (2)	0.019 (3)	0.002 (2)
C13	0.033 (3)	0.021 (2)	0.025 (3)	−0.002 (2)	0.009 (2)	0.006 (2)
C14	0.042 (3)	0.019 (3)	0.042 (3)	0.009 (2)	0.019 (3)	−0.001 (2)
C15	0.053 (4)	0.027 (3)	0.038 (3)	0.008 (2)	0.026 (3)	0.002 (2)
C16	0.053 (4)	0.025 (3)	0.046 (4)	0.005 (2)	0.032 (3)	0.008 (3)
C17	0.026 (3)	0.019 (2)	0.025 (3)	0.0048 (19)	0.008 (2)	0.003 (2)
C18	0.048 (3)	0.020 (2)	0.042 (3)	−0.006 (2)	0.032 (3)	0.001 (2)
C19	0.032 (3)	0.031 (3)	0.018 (3)	0.003 (2)	0.005 (2)	−0.001 (2)
C20	0.034 (3)	0.018 (2)	0.032 (3)	−0.001 (2)	0.012 (3)	−0.006 (2)
Fe1	0.0252 (4)	0.0184 (4)	0.0213 (4)	−0.0012 (3)	0.0075 (3)	0.0002 (3)
N1	0.024 (2)	0.027 (2)	0.024 (2)	−0.0009 (17)	0.0062 (18)	−0.0084 (18)
N2	0.034 (2)	0.0190 (19)	0.023 (2)	−0.0005 (17)	0.0102 (19)	0.0027 (17)
N3	0.0198 (19)	0.0190 (19)	0.018 (2)	−0.0029 (15)	0.0035 (16)	0.0009 (16)
N4	0.029 (2)	0.0165 (19)	0.028 (2)	0.0000 (16)	0.0131 (19)	0.0017 (17)
N5	0.044 (3)	0.033 (2)	0.038 (3)	0.002 (2)	0.017 (2)	0.004 (2)
N6	0.028 (2)	0.022 (2)	0.032 (3)	−0.0008 (17)	0.002 (2)	−0.0096 (18)
S1	0.0507 (9)	0.0343 (8)	0.0475 (9)	−0.0017 (6)	0.0279 (8)	0.0099 (7)
S2	0.0352 (9)	0.0469 (9)	0.0526 (11)	0.0060 (7)	−0.0051 (8)	−0.0199 (8)

C1—N1	1.350 (6)	C12—H12A	0.9900
C1—C2	1.393 (8)	C12—H12B	0.9900
C1—H1	0.9500	C13—N3	1.349 (6)
C2—C3	1.372 (10)	C13—C14	1.377 (7)
C2—H2	0.91 (5)	C13—H13	0.9500
C3—C4	1.367 (9)	C14—C15	1.373 (8)
C3—H3	0.9500	C14—H14	0.98 (5)
C4—C5	1.409 (7)	C15—C16	1.376 (7)
C4—H4	0.9500	C15—H15	0.9500
C5—N1	1.332 (7)	C16—C17	1.378 (7)
C5—C6	1.506 (7)	C16—H16	0.87 (5)
C6—N4	1.476 (6)	C17—N3	1.341 (6)
C6—H6A	0.91 (5)	C17—C18	1.504 (6)
C6—H6B	0.88 (5)	C18—N4	1.477 (6)
C7—N2	1.330 (7)	C18—H18A	0.9900
C7—C8	1.396 (8)	C18—H18B	0.9900
C7—H7	0.96 (5)	C19—N5	1.172 (7)
C8—C9	1.361 (9)	C19—S1	1.623 (5)
C8—H8	0.97 (5)	C20—N6	1.172 (7)
C9—C10	1.373 (8)	C20—S2	1.626 (6)
C9—H9	0.9500	Fe1—N1	2.185 (4)
C10—C11	1.385 (7)	Fe1—N2	2.197 (4)
C10—H10	0.9500	Fe1—N3	2.199 (4)
C11—N2	1.341 (6)	Fe1—N4	2.241 (4)
C11—C12	1.509 (7)	Fe1—N5	2.054 (5)
C12—N4	1.485 (6)	Fe1—N6	2.089 (4)
N1—C1—C2	122.2 (5)	C14—C15—H15	120.9
N1—C1—H1	118.9	C16—C15—H15	120.9
C2—C1—H1	118.9	C15—C16—C17	120.0 (5)
C3—C2—C1	118.8 (6)	C15—C16—H16	120 (3)
C3—C2—H2	125 (4)	C17—C16—H16	119 (3)
C1—C2—H2	115 (4)	N3—C17—C16	122.3 (4)
C4—C3—C2	119.8 (6)	N3—C17—C18	115.1 (4)
C4—C3—H3	120.1	C16—C17—C18	122.6 (4)
C2—C3—H3	120.1	N4—C18—C17	110.2 (4)
C3—C4—C5	118.6 (6)	N4—C18—H18A	109.6
C3—C4—H4	120.7	C17—C18—H18A	109.6
C5—C4—H4	120.7	N4—C18—H18B	109.6
N1—C5—C4	122.3 (5)	C17—C18—H18B	109.6
N1—C5—C6	118.3 (4)	H18A—C18—H18B	108.1
C4—C5—C6	119.2 (5)	N5—C19—S1	179.1 (5)
N4—C6—C5	114.7 (4)	N6—C20—S2	178.7 (5)
N4—C6—H6A	111 (3)	N5—Fe1—N6	96.34 (18)
C5—C6—H6A	111 (3)	N5—Fe1—N1	92.51 (18)
N4—C6—H6B	103 (3)	N6—Fe1—N1	170.87 (16)
C5—C6—H6B	113 (3)	N5—Fe1—N2	105.47 (17)
H6A—C6—H6B	102 (5)	N6—Fe1—N2	91.73 (15)
N2—C7—C8	122.2 (5)	N1—Fe1—N2	83.71 (15)
N2—C7—H7	119 (3)	N5—Fe1—N3	103.16 (16)
C8—C7—H7	119 (3)	N6—Fe1—N3	91.49 (15)
C9—C8—C7	118.8 (6)	N1—Fe1—N3	88.68 (14)
C9—C8—H8	119 (3)	N2—Fe1—N3	150.64 (14)
C7—C8—H8	121 (3)	N5—Fe1—N4	170.32 (17)
C8—C9—C10	119.7 (5)	N6—Fe1—N4	93.18 (16)
C8—C9—H9	120.2	N1—Fe1—N4	78.06 (15)
C10—C9—H9	120.2	N2—Fe1—N4	75.94 (14)
C9—C10—C11	118.6 (5)	N3—Fe1—N4	74.74 (14)
C9—C10—H10	120.7	C5—N1—C1	118.2 (5)
C11—C10—H10	120.7	C5—N1—Fe1	116.0 (3)
N2—C11—C10	122.4 (5)	C1—N1—Fe1	125.3 (4)
N2—C11—C12	115.6 (4)	C7—N2—C11	118.3 (4)
C10—C11—C12	121.8 (4)	C7—N2—Fe1	125.5 (3)
N4—C12—C11	110.9 (4)	C11—N2—Fe1	116.0 (3)
N4—C12—H12A	109.5	C17—N3—C13	117.3 (4)
C11—C12—H12A	109.5	C17—N3—Fe1	115.5 (3)
N4—C12—H12B	109.5	C13—N3—Fe1	127.2 (3)
C11—C12—H12B	109.5	C6—N4—C18	111.0 (4)
H12A—C12—H12B	108.1	C6—N4—C12	111.9 (4)
N3—C13—C14	122.9 (4)	C18—N4—C12	111.0 (4)
N3—C13—H13	118.5	C6—N4—Fe1	110.6 (3)
C14—C13—H13	118.5	C18—N4—Fe1	105.3 (3)
C15—C14—C13	119.3 (5)	C12—N4—Fe1	106.9 (3)
C15—C14—H14	120 (3)	C19—N5—Fe1	168.1 (4)
C13—C14—H14	121 (3)	C20—N6—Fe1	165.9 (4)
C14—C15—C16	118.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S2i	0.95	2.98	3.725 (6)	136
C12—H12B···S2ii	0.99	2.89	3.850 (5)	164
C18—H18B···S1ii	0.99	2.97	3.635 (5)	126

Table 1

Selected bond lengths (Å)

Fe1—N1	2.185 (4)
Fe1—N2	2.197 (4)
Fe1—N3	2.199 (4)
Fe1—N4	2.241 (4)
Fe1—N5	2.054 (5)
Fe1—N6	2.089 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯S2i	0.95	2.98	3.725 (6)	136
C12—H12B⋯S2ii	0.99	2.89	3.850 (5)	164
C18—H18B⋯S1ii	0.99	2.97	3.635 (5)	126

Symmetry codes: (i) ; (ii) .