Bis­(thio­cyanato-κN)[tris(pyridin-2-yl­meth­yl)amine-κ4N]­iron(II)

Dai, J.-W.; Li, Z.-Y.; Sato, O.

doi:10.1107/S1600536813034818

metal-organic compounds

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Volume 70| Part 2| February 2014| Page m35

doi:10.1107/S1600536813034818

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Bis(thiocyanato-κN)[tris(pyridin-2-ylmethyl)amine-κ⁴N]iron(II)

Jing-Wei Dai,^a Zhao-Yang Li ^b and Osamu Sato ^a ^*

^aInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan, and ^bDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan
^*Correspondence e-mail: sato@cm.kyushu-u.ac.jp

(Received 26 December 2013; accepted 29 December 2013; online 8 January 2014)

In the title complex, [Fe(NCS)₂(C₁₈H₁₈N₄)], the Fe^II cation is chelated by a tris(2-pyridylmethyl)amine ligand and coordinated by two thiocyanate anions in a distorted N₆ octahedral geometry. In the crystal, weak C—H⋯S hydrogen bonds and π–π stacking interactions between parallel pyridine rings of adjacent molecules [centroid–centroid distance = 3.653 (3) Å] link the molecules into a two-dimensional supramolecular architecture. The structure contains voids of 124 (9) Å³, which are free of solvent molecules.

CCDC reference: 979003

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_r = 462.37
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.203
S = 1.11
4456 reflections
283 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 979003

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813034818/xu5762sup1.cif

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

checkCIF report

Comment top

A series of iron complexes with the tris(2-pyridylmethyl)amine (tpa) ligands (Benhamou et al., 2008; Boldog et al., 2009; Li et al., 2010; Min et al., 2008; Phan et al., 2012; Wei et al., 2011) that exhibit interesting magnetic properties have been synthesized and structurally characterized. In these complexes, the tpa ligands coordinate to the metal centers through its pyridyl nitrogen atoms and arylamine nitrogen atom. It should be noted that the magnetic behavior of the Fe(II) spin crossover complex with the ligand tpa and thiocyanato has already been reported (Boldog et al., 2009; Li et al., 2010).

In the title compound, Fe(C₁₈H₁₈N₄)(NCS)₂, the Fe(II) atom is coordinated by six nitrogen atoms (Fig. 1). The Fe-N distances range from 2.054 (5) to 2.241 (4) Å. In the crystal, π-π stacking 3.653 (3) Å between parallel pyridine rings and weak C—H···S hydrogen bonds link the molecules into the two dimensional supramolecular structure (Fig. 2).

Related literature top

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 top

A mixture of FeSO₄.7H₂O (0.0281 g, 0.1 mmol), tris(2-pyridylmethyl)amine (tpa, 0.0291 g, 0.1 mmol), KSCN (0.0194 g, 0.2 mmol) and MeOH (5 mL) were sealed in a 25 mL Teflon reactor and heated at 160^oC for 48 h, and then cooled to ambient temperature at a rate of ca. 10 ^oC h^-1 to give yellow block crystals (yield: 21%, based on tpa).

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title complex. Intermolecular C—H···S hydrogen bonds are shown as red dashed lines, and π–π stacking interactions between pyridine rings are shown as blue dashed lines.

Bis(thiocyanato-κN)[tris(pyridin-2-ylmethyl)amine-κ⁴N]iron(II) top

Crystal data top

[Fe(NCS)₂(C₁₈H₁₈N₄)]	F(000) = 1904
M_r = 462.37	D_x = 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

Data collection top

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

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)] = 0.069	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(F_o²) + (0.0906P)² + 9.7621P] where P = (F_o² + 2F_c²)/3
4456 reflections	(Δ/σ)_max < 0.001
283 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Fe(NCS)₂(C₁₈H₁₈N₄)]	V = 4543.0 (18) Å³
M_r = 462.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.714 (5) Å	µ = 0.87 mm⁻¹
b = 11.827 (2) Å	T = 123 K
c = 17.580 (3) Å	0.20 × 0.20 × 0.10 mm
β = 112.87 (3)°

Data collection top

Rigaku Saturn70 diffractometer	4456 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	3275 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.92	R_int = 0.059
10256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.42 e Å⁻³
4456 reflections	Δρ_min = −0.47 e Å⁻³
283 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S2ⁱ	0.95	2.98	3.725 (6)	136.4
C12—H12B···S2ⁱⁱ	0.99	2.89	3.850 (5)	163.8
C18—H18B···S1ⁱⁱ	0.99	2.97	3.635 (5)	125.6

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

Acknowledgements

The authors would like to thank the China Scholarship Council (CSC).

References

Benhamou, L., Lachkar, M., Mandon, D. & Welter, R. (2008). Dalton Trans. pp. 6996–7003. Web of Science CSD CrossRef Google Scholar
Boldog, I., Munoz-Lara, F. J., Gaspar, A. B., Munoz, M. C., Seredyuk, M. & Real, J. A. (2009). Inorg. Chem. 48, 3710–3719. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, B., Wei, R. J., Tao, J., Huang, R. B., Zheng, L. S. & Zheng, Z. P. (2010). J. Am. Chem. Soc. 132, 1558–1566. Web of Science CSD CrossRef CAS PubMed Google Scholar
Min, K. S., Swierczek, K., DiPasquale, A. G., Rheingold, A. L., Reiff, W. M., Arif, A. M. & Miller, J. S. (2008). Chem. Commun. pp. 317–319. Web of Science CSD CrossRef Google Scholar
Phan, H. V., Chakraborty, P., Chen, M. M., Calm, Y. M., Kovnir, K., Keniley, L. K., Hoyt, J. M., Knowles, E. S., Besnard, C., Meisel, M. W., Hauser, A., Achim, C. & Shatruk, M. (2012). Chem. Eur. J. 18, 15805–15815. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, R.-J., Tao, J., Huang, R.-B. & Zheng, L.-S. (2011). Inorg. Chem. 50, 8553–8564. Web of Science CSD CrossRef CAS PubMed Google Scholar