Trichlorido[(meth­yl{2-[meth­yl(2-pyridyl­meth­yl)amino]eth­yl}amino)acetonitrile]iron(III) methanol hemisolvate

Nielsen, A.; McKenzie, C.J.; Bond, A.D.

doi:10.1107/S160053680904375X

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1437

https://doi.org/10.1107/S160053680904375X

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Trichlorido[(methyl{2-[methyl(2-pyridylmethyl)amino]ethyl}amino)acetonitrile]iron(III) methanol hemisolvate

Anne Nielsen,^a Christine J. McKenzie ^a and Andrew D. Bond ^a ^*

^aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense M, Denmark
^*Correspondence e-mail: adb@chem.sdu.dk

(Received 12 October 2009; accepted 22 October 2009; online 28 October 2009)

The title compound, [FeCl₃(C₁₂H₁₈N₄)]·0.5CH₃OH, contains an Fe^III ion in a distorted octahedral coordination environment. The neutral N,N′,N′′-tridentate ligand adopts a fac coordination mode, and chloride ligands lie trans to each of the three coordinated N atoms. In the crystal, the complexes form columns extending parallel to the approximate local threefold axes of the FeN₃Cl₃ octahedra, and the columns are arranged so that the uncoordinated nitrile groups align in an antiparallel manner and the pyridyl rings form offset face-to-face arrangements [interplanar separations = 2.95 (1) and 3.11 (1) Å; centroid–centroid distances = 5.31 (1) and 4.92 (1) Å]. The methanol solvent molecule is disordered about a twofold rotation axis.

Related literature

For structures of similar Fe^III complexes, see: Cowdell et al. (2004 ); Sundaravel et al. (2008 ); Velusamy et al. (2005 ).

Experimental

Crystal data

[FeCl₃(C₁₂H₁₈N₄)]·0.5CH₄O
M_r = 396.53
Monoclinic, C 2/c
a = 34.243 (2) Å
b = 7.1331 (5) Å
c = 15.4835 (11) Å
β = 116.733 (3)°
V = 3377.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 180 K
0.18 × 0.10 × 0.10 mm

Data collection

Bruker–Nonius X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.744, T_max = 0.875
38084 measured reflections
2937 independent reflections
2033 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.07
2937 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe1—N1	2.186 (3)
Fe1—N2	2.235 (3)
Fe1—N3	2.330 (3)
Fe1—Cl1	2.2873 (11)
Fe1—Cl2	2.2908 (11)
Fe1—Cl3	2.3284 (11)

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680904375X/hb5138sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904375X/hb5138Isup2.hkl

checkCIF report

Comment top

The ligand N,N'-dimethyl-N-(2-pyridylmethyl)ethylendiamine- N'-acetonitrile was prepared as a by-product during synthesis of N,N'-dimethyl-N-(2-pyridylmethyl)ethylendiamine- N'-acetic acid, as a result of contamination of the reagent bromoacetic acid with bromoacetonitrile.

Related literature top

For structures of similar Fe^III complexes, see: Cowdell et al. (2004); Sundaravel et al. (2008); Velusamy et al. (2005).

Experimental top

The ligand synthesis was undertaken in three steps:

(i) Picolinal (2.50 ml, 24 mmol) and N,N'-dimethylethylenediamine (2.22 ml, 24 mmol) in dry diethylether (20 ml) were stirred overnight under CaCl₂ protection. The solvent was removed under reduced pressure to leave 1,3-dimethyl-2-(2-pyridylmethyl)imidazolidine as a thin yellow oil (3.9 g, yield 92%).

(ii) NaBH₃CN (1.3925 g, 22 mmol) and CF₃COOH (3.365 ml, 44 mmol) were added in small portions [CAUTION: possible formation of HCN!] to 1,3-dimethyl-2-(2-pyridylmethyl)imidazolidine (3.8944 g, 22 mmol) in methanol (80 ml) and the reaction mixture was stirred overnight under CaCl₂ protection. NaOH (85 ml of a 4 M aqueous solution) was added. The reaction mixture was stirred overnight and extracted with CHCl₂ (3 × 20 ml), then the organic phase was dried over Na₂SO₄ and filtered. The filtrate was evaporated in vacuo to leave N,N'-dimethyl-N-(2-pyridylmethyl)ethylenediamine as a thin yellow oil (3.2 g, yield 81%).

(iii) A mixture of N,N'-dimethyl-N-(2-pyridylmethyl)ethylenediamine (3.1602 g, 18 mmol), bromoacetic acid (2.4499 g, 18 mmol) and triethylamine (2.444 ml, 18 mmol) in absolute ethanol (10 ml) was heated overnight under reflux and N₂. The solvent was removed under reduced pressure, then the residue was re-dissolved in water, adjusted to pH 8 with conc. NaOH and washed with CH₂Cl₂ (3 × 15 ml). The aqueous phase was adjusted to pH 4 with conc. HCl then evaporated in vacuo to leave a mixture of N,N'-dimethyl-N-(2-pyridylmethyl)ethylendiamine- N'-acetonitrile (L) and N,N'-dimethyl-N-(2-pyridylmethyl)ethylendiamine- N'-acetic acid as a brown oil (6.0 g, yield 139% due to impurities of triethylammonium bromide).

The title compound was then prepared as follows:

Anhydrous FeCl₃ (15.8 mg, 0.097 mmol) was added to the mixed ligand product from above (23.3 mg, 0.098 mmol) in methanol (1.75 ml), and a few yellow blocks of (I) were deposited overnight.

Structure description top

For structures of similar Fe^III complexes, see: Cowdell et al. (2004); Sundaravel et al. (2008); Velusamy et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of (I) with displacement ellipsoids shown at 50% probability for non-H atoms. The methanol molecule (C1S—O1S) is disordered around a 2-fold rotation axis.
	Fig. 2. Unit-cell contents of (I) projected along the b axis, which corresponds to the stacking directions of the "columns" referred to in the Abstract.

Trichlorido[(methyl{2-[methyl(2- pyridylmethyl)amino]ethyl}amino)acetonitrile]iron(III) methanol hemisolvate top

Crystal data top

[FeCl₃(C₁₂H₁₈N₄)]·0.5CH₄O	F(000) = 1632
M_r = 396.53	D_x = 1.559 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5350 reflections
a = 34.243 (2) Å	θ = 2.6–21.6°
b = 7.1331 (5) Å	µ = 1.37 mm⁻¹
c = 15.4835 (11) Å	T = 180 K
β = 116.733 (3)°	Block, yellow
V = 3377.8 (4) Å³	0.18 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker–Nonius X8 APEXII CCD diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Thin–slice ω and φ scans	θ_max = 25.0°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −37→40
T_min = 0.744, T_max = 0.875	k = −8→8
38084 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0478P)² + 6.352P] where P = (F_o² + 2F_c²)/3
2937 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[FeCl₃(C₁₂H₁₈N₄)]·0.5CH₄O	V = 3377.8 (4) Å³
M_r = 396.53	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 34.243 (2) Å	µ = 1.37 mm⁻¹
b = 7.1331 (5) Å	T = 180 K
c = 15.4835 (11) Å	0.18 × 0.10 × 0.10 mm
β = 116.733 (3)°

Data collection top

Bruker–Nonius X8 APEXII CCD diffractometer	2937 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2033 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.875	R_int = 0.066
38084 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.07	Δρ_max = 0.48 e Å⁻³
2937 reflections	Δρ_min = −0.45 e Å⁻³
196 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	Occ. (<1)
Fe1	0.132445 (17)	0.50145 (7)	0.14178 (4)	0.02864 (18)
Cl1	0.19634 (3)	0.65429 (14)	0.23597 (8)	0.0446 (3)
Cl2	0.09339 (3)	0.60710 (15)	0.21941 (7)	0.0419 (3)
Cl3	0.10936 (3)	0.71324 (14)	0.01386 (7)	0.0449 (3)
N1	0.07912 (9)	0.3232 (4)	0.0431 (2)	0.0303 (7)
N2	0.16333 (9)	0.3137 (4)	0.0744 (2)	0.0301 (7)
N3	0.15694 (10)	0.2550 (4)	0.2523 (2)	0.0310 (7)
C1	0.03944 (12)	0.3100 (5)	0.0400 (3)	0.0362 (10)
H1A	0.0349	0.3647	0.0907	0.043*
C2	0.00547 (13)	0.2210 (6)	−0.0332 (3)	0.0425 (11)
H2A	−0.0225	0.2177	−0.0343	0.051*
C3	0.01180 (14)	0.1367 (6)	−0.1051 (3)	0.0476 (11)
H3A	−0.0115	0.0715	−0.1557	0.057*
C4	0.05248 (14)	0.1471 (6)	−0.1034 (3)	0.0439 (11)
H4A	0.0576	0.0897	−0.1527	0.053*
C5	0.08561 (12)	0.2433 (5)	−0.0281 (3)	0.0334 (9)
C6	0.12956 (13)	0.2725 (6)	−0.0253 (3)	0.0373 (10)
H6A	0.1379	0.1584	−0.0494	0.045*
H6B	0.1279	0.3779	−0.0684	0.045*
C7	0.20174 (12)	0.3989 (6)	0.0690 (3)	0.0399 (10)
H7A	0.2138	0.3098	0.0392	0.060*
H7B	0.2241	0.4296	0.1344	0.060*
H7C	0.1927	0.5134	0.0300	0.060*
C8	0.17688 (12)	0.1338 (5)	0.1299 (3)	0.0339 (9)
H8A	0.2007	0.0754	0.1197	0.041*
H8B	0.1518	0.0460	0.1058	0.041*
C9	0.19227 (12)	0.1686 (5)	0.2357 (3)	0.0310 (9)
H9A	0.2012	0.0485	0.2714	0.037*
H9B	0.2180	0.2528	0.2604	0.037*
C10	0.12260 (14)	0.1127 (6)	0.2399 (3)	0.0462 (11)
H10A	0.1354	0.0147	0.2891	0.069*
H10B	0.1114	0.0564	0.1754	0.069*
H10C	0.0986	0.1739	0.2471	0.069*
C11	0.17554 (14)	0.3223 (6)	0.3534 (3)	0.0466 (11)
H11A	0.1968	0.4236	0.3625	0.056*
H11B	0.1518	0.3759	0.3655	0.056*
C12	0.19758 (15)	0.1724 (7)	0.4245 (3)	0.0495 (12)
N4	0.21605 (14)	0.0568 (6)	0.4803 (3)	0.0660 (12)
C1S	0.0000	0.3867 (12)	0.2500	0.081 (2)
H1S1	−0.0264	0.3589	0.1902	0.122*	0.50
H1S2	0.0177	0.4799	0.2369	0.122*	0.50
H1S3	−0.0084	0.4363	0.2983	0.122*	0.50
O1S	0.0231 (3)	0.2310 (11)	0.2834 (5)	0.103 (3)	0.50
H1S	0.0438	0.2424	0.3402	0.155*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0251 (3)	0.0238 (3)	0.0325 (3)	−0.0011 (2)	0.0090 (2)	−0.0001 (2)
Cl1	0.0361 (6)	0.0348 (6)	0.0520 (7)	−0.0047 (5)	0.0100 (5)	−0.0027 (5)
Cl2	0.0341 (6)	0.0442 (6)	0.0442 (6)	0.0051 (5)	0.0150 (5)	−0.0080 (5)
Cl3	0.0434 (6)	0.0320 (6)	0.0460 (6)	−0.0021 (5)	0.0083 (5)	0.0112 (5)
N1	0.0254 (18)	0.0280 (18)	0.0329 (18)	0.0023 (14)	0.0090 (14)	0.0036 (14)
N2	0.0262 (18)	0.0366 (19)	0.0250 (17)	−0.0030 (14)	0.0095 (14)	−0.0019 (14)
N3	0.0283 (18)	0.0358 (19)	0.0262 (17)	−0.0009 (14)	0.0098 (15)	−0.0019 (14)
C1	0.028 (2)	0.033 (2)	0.045 (2)	−0.0015 (18)	0.014 (2)	0.0012 (19)
C2	0.029 (2)	0.040 (2)	0.048 (3)	0.0003 (19)	0.008 (2)	0.013 (2)
C3	0.033 (3)	0.046 (3)	0.042 (3)	−0.007 (2)	−0.002 (2)	0.004 (2)
C4	0.044 (3)	0.045 (3)	0.029 (2)	−0.004 (2)	0.0046 (19)	−0.0008 (19)
C5	0.032 (2)	0.033 (2)	0.027 (2)	−0.0023 (17)	0.0048 (19)	0.0036 (18)
C6	0.038 (2)	0.046 (2)	0.027 (2)	−0.0031 (19)	0.0134 (19)	−0.0022 (18)
C7	0.035 (2)	0.048 (3)	0.042 (2)	−0.006 (2)	0.022 (2)	0.000 (2)
C8	0.030 (2)	0.034 (2)	0.035 (2)	0.0039 (18)	0.0116 (18)	−0.0020 (18)
C9	0.029 (2)	0.028 (2)	0.036 (2)	0.0025 (17)	0.0140 (18)	0.0016 (17)
C10	0.042 (3)	0.042 (3)	0.055 (3)	−0.002 (2)	0.022 (2)	0.016 (2)
C11	0.051 (3)	0.049 (3)	0.034 (2)	0.011 (2)	0.014 (2)	−0.002 (2)
C12	0.056 (3)	0.052 (3)	0.041 (3)	0.004 (2)	0.022 (2)	0.005 (2)
N4	0.071 (3)	0.071 (3)	0.054 (3)	0.007 (2)	0.027 (2)	0.017 (2)
C1S	0.073 (6)	0.071 (6)	0.119 (7)	0.000	0.061 (5)	0.000
O1S	0.121 (7)	0.052 (5)	0.074 (6)	0.008 (5)	−0.012 (5)	0.008 (4)

Geometric parameters (Å, º) top

Fe1—N1	2.186 (3)	C6—H6A	0.990
Fe1—N2	2.235 (3)	C6—H6B	0.990
Fe1—N3	2.330 (3)	C7—H7A	0.980
Fe1—Cl1	2.2873 (11)	C7—H7B	0.980
Fe1—Cl2	2.2908 (11)	C7—H7C	0.980
Fe1—Cl3	2.3284 (11)	C8—C9	1.500 (5)
N1—C1	1.341 (5)	C8—H8A	0.990
N1—C5	1.345 (5)	C8—H8B	0.990
N2—C6	1.484 (5)	C9—H9A	0.990
N2—C7	1.484 (4)	C9—H9B	0.990
N2—C8	1.497 (5)	C10—H10A	0.980
N3—C9	1.479 (4)	C10—H10B	0.980
N3—C11	1.480 (5)	C10—H10C	0.980
N3—C10	1.499 (5)	C11—C12	1.476 (6)
C1—C2	1.362 (5)	C11—H11A	0.990
C1—H1A	0.950	C11—H11B	0.990
C2—C3	1.365 (6)	C12—N4	1.155 (5)
C2—H2A	0.950	C1S—O1S	1.326 (9)
C3—C4	1.383 (6)	C1S—H1S1	0.980
C3—H3A	0.950	C1S—H1S2	0.980
C4—C5	1.388 (5)	C1S—H1S3	0.980
C4—H4A	0.950	O1S—O1Sⁱ	1.449 (16)
C5—C6	1.501 (5)	O1S—H1S	0.850

N1—Fe1—N2	75.33 (11)	N2—C6—H6A	109.4
N1—Fe1—Cl1	169.08 (9)	C5—C6—H6A	109.4
N2—Fe1—Cl1	93.76 (8)	N2—C6—H6B	109.4
N1—Fe1—Cl2	93.27 (8)	C5—C6—H6B	109.4
N2—Fe1—Cl2	162.33 (8)	H6A—C6—H6B	108.0
Cl1—Fe1—Cl2	97.20 (4)	N2—C7—H7A	109.5
N1—Fe1—Cl3	85.73 (8)	N2—C7—H7B	109.5
N2—Fe1—Cl3	92.44 (8)	H7A—C7—H7B	109.5
Cl1—Fe1—Cl3	95.42 (4)	N2—C7—H7C	109.5
Cl2—Fe1—Cl3	100.25 (4)	H7A—C7—H7C	109.5
N1—Fe1—N3	89.21 (10)	H7B—C7—H7C	109.5
N2—Fe1—N3	78.53 (10)	N2—C8—C9	110.6 (3)
Cl1—Fe1—N3	88.06 (8)	N2—C8—H8A	109.5
Cl2—Fe1—N3	88.00 (8)	C9—C8—H8A	109.5
Cl3—Fe1—N3	170.54 (8)	N2—C8—H8B	109.5
C1—N1—C5	118.7 (3)	C9—C8—H8B	109.5
C1—N1—Fe1	125.4 (3)	H8A—C8—H8B	108.1
C5—N1—Fe1	115.2 (2)	N3—C9—C8	110.2 (3)
C6—N2—C7	108.6 (3)	N3—C9—H9A	109.6
C6—N2—C8	108.8 (3)	C8—C9—H9A	109.6
C7—N2—C8	109.2 (3)	N3—C9—H9B	109.6
C6—N2—Fe1	107.1 (2)	C8—C9—H9B	109.6
C7—N2—Fe1	113.4 (2)	H9A—C9—H9B	108.1
C8—N2—Fe1	109.6 (2)	N3—C10—H10A	109.5
C9—N3—C11	108.8 (3)	N3—C10—H10B	109.5
C9—N3—C10	110.5 (3)	H10A—C10—H10B	109.5
C11—N3—C10	107.1 (3)	N3—C10—H10C	109.5
C9—N3—Fe1	103.9 (2)	H10A—C10—H10C	109.5
C11—N3—Fe1	111.9 (2)	H10B—C10—H10C	109.5
C10—N3—Fe1	114.5 (2)	C12—C11—N3	112.8 (3)
N1—C1—C2	122.3 (4)	C12—C11—H11A	109.0
N1—C1—H1A	118.9	N3—C11—H11A	109.0
C2—C1—H1A	118.9	C12—C11—H11B	109.0
C1—C2—C3	119.6 (4)	N3—C11—H11B	109.0
C1—C2—H2A	120.2	H11A—C11—H11B	107.8
C3—C2—H2A	120.2	N4—C12—C11	177.8 (5)
C2—C3—C4	119.3 (4)	O1S—C1S—H1S1	109.5
C2—C3—H3A	120.4	O1S—C1S—H1S2	109.5
C4—C3—H3A	120.4	H1S1—C1S—H1S2	109.5
C3—C4—C5	118.5 (4)	O1S—C1S—H1S3	109.5
C3—C4—H4A	120.7	H1S1—C1S—H1S3	109.5
C5—C4—H4A	120.7	H1S2—C1S—H1S3	109.5
N1—C5—C4	121.6 (4)	C1S—O1S—O1Sⁱ	56.9 (4)
N1—C5—C6	116.8 (3)	C1S—O1S—H1S	113.4
C4—C5—C6	121.5 (4)	O1Sⁱ—O1S—H1S	150.8
N2—C6—C5	111.1 (3)

N2—Fe1—N1—C1	168.7 (3)	Cl2—Fe1—N3—C11	−51.8 (2)
Cl1—Fe1—N1—C1	165.9 (3)	N1—Fe1—N3—C10	−22.9 (3)
Cl2—Fe1—N1—C1	2.4 (3)	N2—Fe1—N3—C10	−98.1 (3)
Cl3—Fe1—N1—C1	−97.6 (3)	Cl1—Fe1—N3—C10	167.7 (3)
N3—Fe1—N1—C1	90.4 (3)	Cl2—Fe1—N3—C10	70.4 (2)
N2—Fe1—N1—C5	−21.2 (2)	C5—N1—C1—C2	−0.9 (5)
Cl1—Fe1—N1—C5	−24.1 (6)	Fe1—N1—C1—C2	168.8 (3)
Cl2—Fe1—N1—C5	172.5 (2)	N1—C1—C2—C3	2.0 (6)
Cl3—Fe1—N1—C5	72.4 (2)	C1—C2—C3—C4	−1.6 (6)
N3—Fe1—N1—C5	−99.6 (3)	C2—C3—C4—C5	0.1 (6)
N1—Fe1—N2—C6	32.1 (2)	C1—N1—C5—C4	−0.6 (5)
Cl1—Fe1—N2—C6	−148.5 (2)	Fe1—N1—C5—C4	−171.3 (3)
Cl2—Fe1—N2—C6	83.2 (3)	C1—N1—C5—C6	176.0 (3)
Cl3—Fe1—N2—C6	−52.9 (2)	Fe1—N1—C5—C6	5.3 (4)
N3—Fe1—N2—C6	124.3 (2)	C3—C4—C5—N1	1.0 (6)
N1—Fe1—N2—C7	151.8 (3)	C3—C4—C5—C6	−175.5 (4)
Cl1—Fe1—N2—C7	−28.7 (2)	C7—N2—C6—C5	−162.3 (3)
Cl2—Fe1—N2—C7	−157.0 (2)	C8—N2—C6—C5	78.9 (4)
Cl3—Fe1—N2—C7	66.9 (2)	Fe1—N2—C6—C5	−39.5 (4)
N3—Fe1—N2—C7	−116.0 (2)	N1—C5—C6—N2	24.1 (5)
N1—Fe1—N2—C8	−85.8 (2)	C4—C5—C6—N2	−159.3 (4)
Cl1—Fe1—N2—C8	93.7 (2)	C6—N2—C8—C9	−152.1 (3)
Cl2—Fe1—N2—C8	−34.7 (4)	C7—N2—C8—C9	89.5 (4)
Cl3—Fe1—N2—C8	−170.7 (2)	Fe1—N2—C8—C9	−35.3 (3)
N3—Fe1—N2—C8	6.4 (2)	C11—N3—C9—C8	−168.7 (3)
N1—Fe1—N3—C9	97.7 (2)	C10—N3—C9—C8	74.0 (4)
N2—Fe1—N3—C9	22.5 (2)	Fe1—N3—C9—C8	−49.3 (3)
Cl1—Fe1—N3—C9	−71.7 (2)	N2—C8—C9—N3	59.5 (4)
Cl2—Fe1—N3—C9	−169.0 (2)	C9—N3—C11—C12	−56.6 (4)
N1—Fe1—N3—C11	−145.1 (3)	C10—N3—C11—C12	62.9 (4)
N2—Fe1—N3—C11	139.7 (3)	Fe1—N3—C11—C12	−170.8 (3)
Cl1—Fe1—N3—C11	45.5 (2)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[FeCl₃(C₁₂H₁₈N₄)]·0.5CH₄O
M_r	396.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	180
a, b, c (Å)	34.243 (2), 7.1331 (5), 15.4835 (11)
β (°)	116.733 (3)
V (Å³)	3377.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.37
Crystal size (mm)	0.18 × 0.10 × 0.10

Data collection
Diffractometer	Bruker–Nonius X8 APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.744, 0.875
No. of measured, independent and observed [I > 2σ(I)] reflections	38084, 2937, 2033
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.07
No. of reflections	2937
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.45

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe1—N1	2.186 (3)	Fe1—Cl1	2.2873 (11)
Fe1—N2	2.235 (3)	Fe1—Cl2	2.2908 (11)
Fe1—N3	2.330 (3)	Fe1—Cl3	2.3284 (11)

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cowdell, R., Davies, C. J., Hilton, S. T., Marechal, J.-D., Solan, G. A., Thomas, O. & Fawcett, J. (2004). Dalton Trans. pp. 3231–3240. Web of Science CSD CrossRef Google Scholar
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Sundaravel, K., Dhanalakshmi, T., Suresh, E. & Palaniandavar, M. (2008). Dalton Trans. pp. 7012–7025. Web of Science CSD CrossRef Google Scholar
Velusamy, M., Mayilmurugan, R. & Palaniandavar, M. (2005). J. Inorg. Biochem. 99, 1032–1042. Web of Science CSD CrossRef PubMed CAS Google Scholar

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