catena-Poly[[[di­aqua­bis­(seleno­cyanato-κN)iron(II)]-μ-1,2-bis­(pyridin-4-yl)ethane-κ2N:N′] 1,2-bis­(pyridin-4-yl)ethane disolvate dihydrate]

Wöhlert, S.; Jess, I.; Näther, C.

doi:10.1107/S1600536813012312

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages m320-m321

doi:10.1107/S1600536813012312

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catena-Poly[[[diaquabis(selenocyanato-κN)iron(II)]-μ-1,2-bis(pyridin-4-yl)ethane-κ²N:N′] 1,2-bis(pyridin-4-yl)ethane disolvate dihydrate]

Susanne Wöhlert,^a ^* Inke Jess ^a and Christian Näther ^a

^aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
^*Correspondence e-mail: swoehlert@ac.uni-kiel.de

(Received 2 May 2013; accepted 6 May 2013; online 15 May 2013)

The title compound, {[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O}_n, was obtained by the reaction of iron(II) sulfate heptahydrate and potassium selenocyanate with 1,2-bis(pyridin-4-yl)ethane (bpa) in water. The Fe^II cation is coordinated by two N-bonded selenocyanate anions, two water molecules and two 1,2-bis(pyridin-4-yl)ethane (bpa) ligands in a slightly distorted octahedral geometry. In addition, two non-coordinating bpa molecules and two water molecules are present. The Fe^II cation is located on a center of inversion while the coordinating bpa ligand is located on a twofold rotation axis. The Fe^II cations are linked by the bpa ligands into chains along the b-axis direction, which are further connected into layers perpedicular to the c axis by O—H⋯N and O—H⋯O hydrogen bonds to the non-coordinating bpa and the water molecules. The crystal studied was twinned by pseudo-merohedry (180° rotation along c*; contribution of the minor twin component 3.7%).

Related literature

For background to this work see: Boeckmann & Näther (2011 ); Wöhlert et al. (2012 ); Boeckmann et al. (2012 ).

Experimental

Crystal data

[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O
M_r = 890.58
Monoclinic, P 2₁ /c
a = 8.0790 (6) Å
b = 14.1870 (7) Å
c = 17.6553 (12) Å
β = 102.645 (8)°
V = 1974.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.28 mm⁻¹
T = 293 K
0.23 × 0.16 × 0.09 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.645, T_max = 0.818
20183 measured reflections
4540 independent reflections
3659 reflections with I > 2σ(I)
R_int = 0.095

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.09
4540 reflections
242 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe1—O1	2.069 (3)
Fe1—N1	2.132 (3)
Fe1—N10	2.347 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.82	1.89	2.696 (4)	166
O1—H2O1⋯O2ⁱ	0.82	1.87	2.672 (4)	165
O2—H1O2⋯N20ⁱⁱ	0.82	1.98	2.688 (4)	144
O2—H2O2⋯N21ⁱⁱⁱ	0.82	1.92	2.682 (4)	155
Symmetry codes: (i) -x+3, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+2, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: XCIF in SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813012312/zl2548sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012312/zl2548Isup2.hkl

checkCIF report

Comment top

In our recent work we have reported on the synthesis and characterization of cobalt(II) and iron(II) selenocyanate coordination polymers that show coexistence of metamagnetism and a slow relaxation of the magnetization (Boeckmann & Näther, 2011; Wöhlert et al., 2012 and Boeckmann et al., 2012). These compounds can be prepared by thermal decomposition of suitable precursor compounds that contain volatile ligands like e.g. water in hydrates and therefore, such compounds are of extreme importance for our project. In the course of these investigations we obtained such a precursor based on 1,2-bis(pyridin-4-yl)ethane (bpa), which was characterized by single-crystal X-ray diffraction.

In the crystal structure of the title compound Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]_n^.2C₁₂H₁₂N₂^.2H₂O solvate each Fe^II cation is coordinated by two N-bonded selenocyanate anions, two water molecules and two bpa ligands (Fig. 1). The FeN₄O₂ octahedra are slightly distorted with distances in the range of 2.071 (4) Å to 2.344 (4) Å. The angles arround the Fe^II cations are in the range of 86.91 (16) ° to 93.09 (16) ° and of 180 ° (Tab. 1). Each Fe^II cation is located on a center of inversion while the coordinating bpa ligand is located on a twofold rotation axis. The iron(II) cations are connected by the bpa ligands into one dimensional polymeric chains, which elongate in the direction of the crystallographic b-axis (Fig. 2). These chains are linked by intermolecular O—H···N and O—H···O hydrogen bonding into layers by non-coordinating bpa ligands and water molecules perpedicular to c (Fig. 2, Tab. 2).

Related literature top

For background to this work see: Boeckmann & Näther (2011); Wöhlert et al. (2012); Boeckmann et al. (2012).

Experimental top

FeSO₄×7H₂O, KNCSe and 1,2-bis(pyridin-4-yl)ethane were obtained from Alfa Aesar. All chemicals were used without further purification. 0.15 mmol (43 mg) FeSO₄×7H₂O and 0.2 mmol (28 mg) KNCSe were reacted with 0.6 mmol (109 mg) 1,2-bis(pyridin-4-yl)ethane in 1 ml water. Red single-crystals of the title compound were obtained after three days.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. : Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = -x + 2, -y, -z + 1; ii = -x + 2, -y + 1, -z + 1; iii = x, y - 1, z.
	Fig. 2. : Crystal structure of the title compound with O–H–N and O–H–O hydrogen bonding shown as dashed lines (black = iron, blue = nitrogen, orange = selenium, red = oxygen, grey = carbon, white = hydrogen).

catena-Poly[[[diaquabis(selenocyanato-κN)iron(II)]-µ-1,2-bis(pyridin-4-yl)ethane-κ²N:N'] 1,2-bis(pyridin-4-yl)ethane disolvate dihydrate] top

Crystal data top

[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O	F(000) = 908
M_r = 890.58	D_x = 1.498 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20183 reflections
a = 8.0790 (6) Å	θ = 2.4–27.5°
b = 14.1870 (7) Å	µ = 2.28 mm⁻¹
c = 17.6553 (12) Å	T = 293 K
β = 102.645 (8)°	Block, red
V = 1974.5 (2) Å³	0.23 × 0.16 × 0.09 mm
Z = 2

Data collection top

Stoe IPDS-2 diffractometer	4540 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.095
ω scan	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −10→10
T_min = 0.645, T_max = 0.818	k = −18→18
20183 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0393P)² + 4.2316P] where P = (F_o² + 2F_c²)/3
4540 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O	V = 1974.5 (2) Å³
M_r = 890.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0790 (6) Å	µ = 2.28 mm⁻¹
b = 14.1870 (7) Å	T = 293 K
c = 17.6553 (12) Å	0.23 × 0.16 × 0.09 mm
β = 102.645 (8)°

Data collection top

Stoe IPDS-2 diffractometer	4540 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	3659 reflections with I > 2σ(I)
T_min = 0.645, T_max = 0.818	R_int = 0.095
20183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.09	Δρ_max = 0.58 e Å⁻³
4540 reflections	Δρ_min = −0.88 e Å⁻³
242 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Fe1	1.0000	0.0000	0.5000	0.01501 (15)
N1	1.0298 (4)	−0.0036 (2)	0.62294 (18)	0.0224 (6)
C1	0.9954 (4)	−0.0081 (2)	0.6834 (2)	0.0174 (7)
Se1	0.94592 (5)	−0.01632 (3)	0.77704 (2)	0.02554 (12)
N10	0.9925 (4)	0.16528 (19)	0.50356 (18)	0.0189 (6)
C10	1.0341 (5)	0.2181 (2)	0.4477 (2)	0.0229 (8)
H10	1.0757	0.1878	0.4090	0.028*
C11	1.0186 (5)	0.3159 (2)	0.4442 (2)	0.0246 (8)
H11	1.0494	0.3489	0.4040	0.030*
C12	0.9576 (5)	0.3639 (2)	0.5007 (2)	0.0223 (8)
C13	0.9174 (6)	0.3093 (2)	0.5604 (2)	0.0251 (8)
H13	0.8780	0.3379	0.6004	0.030*
C14	0.9370 (5)	0.2119 (2)	0.5591 (2)	0.0229 (8)
H14	0.9099	0.1770	0.5994	0.027*
C15	0.9243 (6)	0.4693 (2)	0.4954 (3)	0.0353 (11)
H15A	0.8506	0.4826	0.4454	0.042*
H15B	0.8631	0.4864	0.5349	0.042*
N20	0.5764 (5)	0.1671 (2)	0.6762 (2)	0.0319 (8)
C20	0.6829 (6)	0.2156 (3)	0.7307 (3)	0.0319 (9)
H20	0.7699	0.1830	0.7635	0.038*
C21	0.6708 (6)	0.3120 (3)	0.7410 (3)	0.0296 (9)
H21	0.7474	0.3429	0.7801	0.036*
C22	0.5421 (5)	0.3616 (2)	0.6920 (2)	0.0254 (8)
C23	0.4316 (6)	0.3110 (3)	0.6357 (3)	0.0320 (9)
H23	0.3433	0.3414	0.6020	0.038*
C24	0.4532 (6)	0.2150 (3)	0.6300 (3)	0.0342 (10)
H24	0.3775	0.1821	0.5918	0.041*
C25	0.5290 (6)	0.4669 (3)	0.6976 (2)	0.0291 (9)
H25A	0.6028	0.4888	0.7453	0.035*
H25B	0.4135	0.4844	0.6987	0.035*
C26	0.5799 (6)	0.5132 (3)	0.6283 (2)	0.0277 (8)
H26A	0.6899	0.4891	0.6241	0.033*
H26B	0.4986	0.4955	0.5815	0.033*
C27	0.5889 (5)	0.6193 (2)	0.6332 (2)	0.0229 (8)
C28	0.6949 (5)	0.6639 (3)	0.6955 (2)	0.0253 (8)
H28	0.7595	0.6288	0.7359	0.030*
C29	0.7026 (5)	0.7616 (3)	0.6964 (2)	0.0283 (8)
H29	0.7759	0.7909	0.7376	0.034*
C30	0.5083 (7)	0.7723 (3)	0.5820 (3)	0.0365 (10)
H30	0.4436	0.8091	0.5429	0.044*
C31	0.4938 (6)	0.6753 (3)	0.5756 (3)	0.0329 (9)
H31	0.4209	0.6480	0.5332	0.039*
N21	0.6101 (5)	0.8156 (2)	0.6412 (2)	0.0309 (8)
O1	1.2588 (3)	0.00213 (19)	0.50632 (15)	0.0241 (5)
H1O1	1.2976	−0.0004	0.4672	0.036*
H2O1	1.3430	−0.0061	0.5412	0.036*
O2	1.4393 (4)	0.00140 (17)	0.39471 (15)	0.0227 (5)
H1O2	1.3985	−0.0371	0.3612	0.034*
H2O2	1.3942	0.0526	0.3828	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0173 (3)	0.0124 (3)	0.0164 (3)	0.0008 (2)	0.0059 (3)	0.0003 (2)
N1	0.0271 (16)	0.0203 (14)	0.0197 (15)	0.0008 (12)	0.0049 (13)	0.0006 (11)
C1	0.0183 (16)	0.0117 (14)	0.0204 (17)	0.0007 (12)	0.0007 (13)	−0.0002 (11)
Se1	0.0285 (2)	0.03071 (19)	0.01874 (19)	−0.00250 (16)	0.00811 (15)	−0.00011 (14)
N10	0.0242 (15)	0.0135 (13)	0.0199 (14)	0.0008 (11)	0.0067 (12)	0.0008 (10)
C10	0.032 (2)	0.0146 (15)	0.0268 (19)	−0.0005 (14)	0.0168 (17)	−0.0018 (13)
C11	0.034 (2)	0.0159 (15)	0.029 (2)	−0.0030 (14)	0.0198 (18)	0.0026 (13)
C12	0.0263 (19)	0.0118 (15)	0.032 (2)	−0.0015 (13)	0.0132 (17)	−0.0007 (13)
C13	0.037 (2)	0.0166 (16)	0.0266 (19)	0.0007 (15)	0.0166 (17)	−0.0031 (14)
C14	0.034 (2)	0.0151 (15)	0.0214 (17)	0.0023 (14)	0.0110 (16)	0.0017 (13)
C15	0.045 (3)	0.0125 (16)	0.059 (3)	0.0014 (16)	0.034 (2)	−0.0004 (16)
N20	0.044 (2)	0.0205 (15)	0.0312 (18)	0.0000 (14)	0.0075 (17)	−0.0019 (13)
C20	0.034 (2)	0.0256 (19)	0.036 (2)	0.0033 (16)	0.0073 (19)	0.0017 (16)
C21	0.033 (2)	0.0226 (18)	0.034 (2)	−0.0059 (15)	0.0077 (18)	−0.0015 (15)
C22	0.031 (2)	0.0181 (16)	0.032 (2)	−0.0014 (14)	0.0172 (18)	−0.0003 (14)
C23	0.038 (2)	0.0248 (19)	0.032 (2)	0.0006 (16)	0.0034 (19)	0.0013 (15)
C24	0.048 (3)	0.0226 (18)	0.029 (2)	−0.0054 (17)	0.003 (2)	−0.0039 (15)
C25	0.034 (2)	0.0204 (17)	0.037 (2)	−0.0012 (15)	0.0168 (19)	−0.0042 (15)
C26	0.037 (2)	0.0181 (16)	0.030 (2)	0.0010 (15)	0.0115 (18)	−0.0013 (14)
C27	0.0235 (19)	0.0179 (16)	0.029 (2)	0.0002 (13)	0.0098 (16)	−0.0015 (13)
C28	0.025 (2)	0.0213 (17)	0.032 (2)	0.0019 (14)	0.0101 (17)	0.0002 (14)
C29	0.031 (2)	0.0211 (17)	0.034 (2)	−0.0025 (15)	0.0099 (18)	−0.0030 (15)
C30	0.047 (3)	0.0242 (19)	0.037 (2)	0.0062 (18)	0.007 (2)	0.0079 (16)
C31	0.040 (2)	0.0262 (19)	0.030 (2)	−0.0027 (17)	0.0022 (19)	0.0004 (15)
N21	0.040 (2)	0.0194 (15)	0.036 (2)	0.0017 (14)	0.0137 (17)	0.0011 (13)
O1	0.0186 (13)	0.0350 (14)	0.0195 (12)	0.0013 (10)	0.0059 (11)	0.0015 (10)
O2	0.0271 (14)	0.0174 (11)	0.0231 (13)	0.0031 (10)	0.0043 (11)	−0.0012 (9)

Geometric parameters (Å, º) top

Fe1—O1	2.069 (3)	C21—H21	0.9300
Fe1—O1ⁱ	2.069 (3)	C22—C23	1.383 (6)
Fe1—N1ⁱ	2.132 (3)	C22—C25	1.503 (5)
Fe1—N1	2.132 (3)	C23—C24	1.379 (6)
Fe1—N10ⁱ	2.347 (3)	C23—H23	0.9300
Fe1—N10	2.347 (3)	C24—H24	0.9300
N1—C1	1.162 (5)	C25—C26	1.522 (6)
C1—Se1	1.788 (4)	C25—H25A	0.9700
N10—C10	1.339 (5)	C25—H25B	0.9700
N10—C14	1.339 (5)	C26—C27	1.508 (5)
C10—C11	1.393 (5)	C26—H26A	0.9700
C10—H10	0.9300	C26—H26B	0.9700
C11—C12	1.384 (5)	C27—C31	1.383 (6)
C11—H11	0.9300	C27—C28	1.390 (5)
C12—C13	1.402 (5)	C28—C29	1.388 (5)
C12—C15	1.519 (5)	C28—H28	0.9300
C13—C14	1.392 (5)	C29—N21	1.333 (5)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—N21	1.330 (6)
C15—C15ⁱⁱ	1.481 (9)	C30—C31	1.384 (6)
C15—H15A	0.9700	C30—H30	0.9300
C15—H15B	0.9700	C31—H31	0.9300
N20—C24	1.327 (6)	O1—H1O1	0.8201
N20—C20	1.333 (6)	O1—H2O1	0.8201
C20—C21	1.386 (5)	O2—H1O2	0.8199
C20—H20	0.9300	O2—H2O2	0.8200
C21—C22	1.390 (6)

O1—Fe1—O1ⁱ	180.000 (1)	C20—C21—C22	118.9 (4)
O1—Fe1—N1ⁱ	86.68 (12)	C20—C21—H21	120.5
O1ⁱ—Fe1—N1ⁱ	93.32 (12)	C22—C21—H21	120.5
O1—Fe1—N1	93.32 (12)	C23—C22—C21	117.5 (3)
O1ⁱ—Fe1—N1	86.68 (12)	C23—C22—C25	121.3 (4)
N1ⁱ—Fe1—N1	180.000 (1)	C21—C22—C25	121.1 (4)
O1—Fe1—N10ⁱ	89.09 (11)	C24—C23—C22	119.6 (4)
O1ⁱ—Fe1—N10ⁱ	90.91 (11)	C24—C23—H23	120.2
N1ⁱ—Fe1—N10ⁱ	89.69 (11)	C22—C23—H23	120.2
N1—Fe1—N10ⁱ	90.31 (11)	N20—C24—C23	123.4 (4)
O1—Fe1—N10	90.91 (11)	N20—C24—H24	118.3
O1ⁱ—Fe1—N10	89.09 (11)	C23—C24—H24	118.3
N1ⁱ—Fe1—N10	90.31 (11)	C22—C25—C26	109.9 (3)
N1—Fe1—N10	89.69 (11)	C22—C25—H25A	109.7
N10ⁱ—Fe1—N10	180.000 (1)	C26—C25—H25A	109.7
C1—N1—Fe1	160.1 (3)	C22—C25—H25B	109.7
N1—C1—Se1	178.9 (3)	C26—C25—H25B	109.7
C10—N10—C14	116.2 (3)	H25A—C25—H25B	108.2
C10—N10—Fe1	121.8 (2)	C27—C26—C25	113.8 (3)
C14—N10—Fe1	121.8 (2)	C27—C26—H26A	108.8
N10—C10—C11	123.7 (3)	C25—C26—H26A	108.8
N10—C10—H10	118.1	C27—C26—H26B	108.8
C11—C10—H10	118.1	C25—C26—H26B	108.8
C12—C11—C10	120.1 (3)	H26A—C26—H26B	107.7
C12—C11—H11	120.0	C31—C27—C28	117.9 (3)
C10—C11—H11	120.0	C31—C27—C26	121.3 (4)
C11—C12—C13	116.5 (3)	C28—C27—C26	120.8 (3)
C11—C12—C15	121.8 (3)	C29—C28—C27	118.8 (4)
C13—C12—C15	121.6 (3)	C29—C28—H28	120.6
C14—C13—C12	119.4 (3)	C27—C28—H28	120.6
C14—C13—H13	120.3	N21—C29—C28	123.3 (4)
C12—C13—H13	120.3	N21—C29—H29	118.3
N10—C14—C13	124.0 (3)	C28—C29—H29	118.3
N10—C14—H14	118.0	N21—C30—C31	123.3 (4)
C13—C14—H14	118.0	N21—C30—H30	118.3
C15ⁱⁱ—C15—C12	116.2 (5)	C31—C30—H30	118.3
C15ⁱⁱ—C15—H15A	108.2	C27—C31—C30	119.2 (4)
C12—C15—H15A	108.2	C27—C31—H31	120.4
C15ⁱⁱ—C15—H15B	108.2	C30—C31—H31	120.4
C12—C15—H15B	108.2	C30—N21—C29	117.4 (3)
H15A—C15—H15B	107.4	Fe1—O1—H1O1	121.5
C24—N20—C20	117.3 (3)	Fe1—O1—H2O1	134.5
N20—C20—C21	123.4 (4)	H1O1—O1—H2O1	102.6
N20—C20—H20	118.3	H1O2—O2—H2O2	108.6
C21—C20—H20	118.3

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	1.89	2.696 (4)	166
O1—H2O1···O2ⁱⁱⁱ	0.82	1.87	2.672 (4)	165
O2—H1O2···N20ⁱ	0.82	1.98	2.688 (4)	144
O2—H2O2···N21ⁱⁱ	0.82	1.92	2.682 (4)	155

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+3, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O
M_r	890.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0790 (6), 14.1870 (7), 17.6553 (12)
β (°)	102.645 (8)
V (Å³)	1974.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.28
Crystal size (mm)	0.23 × 0.16 × 0.09

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)
T_min, T_max	0.645, 0.818
No. of measured, independent and observed [I > 2σ(I)] reflections	20183, 4540, 3659
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.09
No. of reflections	4540
No. of parameters	242
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.88

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011), XCIF in SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Fe1—O1	2.069 (3)	Fe1—N10	2.347 (3)
Fe1—N1	2.132 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	1.89	2.696 (4)	165.5
O1—H2O1···O2ⁱ	0.82	1.87	2.672 (4)	164.6
O2—H1O2···N20ⁱⁱ	0.82	1.98	2.688 (4)	143.6
O2—H2O2···N21ⁱⁱⁱ	0.82	1.92	2.682 (4)	155.2

Symmetry codes: (i) −x+3, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/5–1) and the State of Schleswig–Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facility.

References

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