Trichlorido[(meth-yl{2-[meth-yl(2-pyridyl-meth-yl)amino]eth-yl}amino)acetonitrile]iron(III) methanol hemisolvate.

The title compound, [FeCl(3)(C(12)H(18)N(4))]·0.5CH(3)OH, contains an Fe(III) ion in a distorted octa-hedral 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 FeN(3)Cl(3) octa-hedra, and the columns are arranged so that the uncoordinated nitrile groups align in an anti-parallel manner and the pyridyl rings form offset face-to-face arrangements [inter-planar separations = 2.95 (1) and 3.11 (1) Å; centroid-centroid distances = 5.31 (1) and 4.92 (1) Å]. The methanol solvent mol-ecule is disordered about a twofold rotation axis.

Related literature

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

Experimental

Crystal data

[FeCl3(C12H18N4)]·0.5CH4O

M = 396.53

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.07

2937 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.45 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904375X/hb5138Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[FeCl3(C12H18N4)]·0.5CH4O	F(000) = 1632
Mr = 396.53	Dx = 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

Bruker–Nonius X8 APEXII CCD diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
graphite	Rint = 0.066
Thin–slice ω and φ scans	θmax = 25.0°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −37→40
Tmin = 0.744, Tmax = 0.875	k = −8→8
38084 measured reflections	l = −18→18

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(Fo2) + (0.0478P)2 + 6.352P] where P = (Fo2 + 2Fc2)/3
2937 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.45 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	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

	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)

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)

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)