{2-[2,2-Bis(4,4-dimethyl-4,5-di-hydro-1,3-oxazol-2-yl-κN)prop-yl]pyridine}-dichlorido-iron(II).

The title compound,[FeCl2(C18H25N3O2)], has a distorted tetra-hedral Cl2N2 coordination of the Fe(II) atom as a result of the constraints imposed by the 2-[2,2-bis-(4,4-dimethyl-4,5-di-hydro-1,3-oxazol-2-yl)prop-yl]pyridine ligand. The pyridine ring is almost perpendicular to the six-membered chelated ring containing the metal atom [dihedral angle between their mean planes = 88.5 (1)°].

Related literature

For the analogous bis­(oxazoline)iron(II) complex, see: Ferro et al. (2007 ▶). For active catalysts used in atom-transfer radical polymerization (ATRP) reactions, see: Matyjaszewski & Xia (2001 ▶); Kamigaito et al. (2001 ▶); De Roma et al. (2011 ▶); Ferro et al. (2009 ▶). For similar salicylaldiminato complexes, see: O‘Reilly et al. (2003 ▶). For structural data on metal complexes, see: Li, Lamberti, Mazzeo et al. (2012 ▶); Li, Lamberti, Roviello et al. (2012 ▶); Busico et al. (2006 ▶); D‘Auria et al. (2012 ▶). For N-rich aromatic heterocycles, see: Carella et al. (2012 ▶), Roviello et al. (2012 ▶); Milione & Bertolasi (2011 ▶).

Experimental

Crystal data

[FeCl2(C18H25N3O2)]

M = 442.16

Monoclinic,

a = 10.102 (2) Å

b = 13.925 (3) Å

c = 14.764 (2) Å

β = 105.27 (1)°

V = 2003.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 173 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.820, T max = 0.903

16483 measured reflections

4578 independent reflections

3033 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.083

S = 1.01

4578 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018047/gg2121sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018047/gg2121Isup2.hkl

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

[FeCl2(C18H25N3O2)]	F(000) = 920
Mr = 442.16	Dx = 1.466 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 186 reflections
a = 10.102 (2) Å	θ = 3.3–21.8°
b = 13.925 (3) Å	µ = 1.04 mm−1
c = 14.764 (2) Å	T = 173 K
β = 105.27 (1)°	Prism, yellow
V = 2003.5 (6) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	4578 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD rotation images, thick slices scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −17→17
Tmin = 0.820, Tmax = 0.903	l = −17→19
16483 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0268P)2 + 1.0658P] where P = (Fo2 + 2Fc2)/3
4578 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.30 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
Fe1	0.89069 (4)	0.34069 (2)	0.30170 (2)	0.01876 (10)
Cl1	0.87074 (7)	0.33484 (5)	0.14547 (4)	0.03170 (17)
Cl2	1.10937 (7)	0.33479 (5)	0.39080 (5)	0.03539 (17)
O1	0.58286 (18)	0.18564 (11)	0.38732 (12)	0.0238 (4)
O2	0.59661 (18)	0.52345 (11)	0.36945 (12)	0.0245 (4)
N1	0.7675 (2)	0.24265 (13)	0.34819 (13)	0.0172 (4)
N3	0.7766 (2)	0.45103 (13)	0.33782 (13)	0.0177 (4)
N2	0.5051 (2)	0.35734 (15)	0.19970 (14)	0.0257 (5)
C1	0.7779 (3)	0.13552 (16)	0.34031 (16)	0.0193 (5)
C2	0.6654 (3)	0.10073 (17)	0.38508 (19)	0.0267 (6)
H2A	0.6096	0.0494	0.3468	0.027*
H2B	0.7059	0.0759	0.4493	0.027*
C3	0.6578 (3)	0.26111 (16)	0.37190 (16)	0.0177 (5)
C4	0.6652 (3)	0.44283 (16)	0.36183 (15)	0.0169 (5)
C5	0.6871 (3)	0.60246 (17)	0.36051 (19)	0.0268 (6)
H5A	0.7304	0.6313	0.4225	0.027*
H5B	0.6359	0.6529	0.3183	0.027*
C6	0.7948 (3)	0.55571 (17)	0.31880 (18)	0.0244 (6)
C7	0.7456 (3)	0.11024 (19)	0.23679 (17)	0.0309 (6)
H7A	0.6525	0.1318	0.2052	0.031*
H7B	0.7518	0.0405	0.2298	0.031*
H7C	0.8116	0.1421	0.2086	0.031*
C8	0.9184 (3)	0.10127 (19)	0.3938 (2)	0.0331 (7)
H8B	0.9881	0.1317	0.3680	0.033*
H8A	0.9237	0.0314	0.3878	0.033*
H8C	0.9348	0.1185	0.4602	0.033*
C9	0.7624 (3)	0.57103 (19)	0.21363 (19)	0.0373 (7)
H9B	0.8259	0.5331	0.1880	0.037*
H9C	0.7726	0.6392	0.2005	0.037*
H9A	0.6680	0.5507	0.1844	0.037*
C10	0.9397 (3)	0.5868 (2)	0.3683 (2)	0.0381 (7)
H10C	0.9567	0.5757	0.4359	0.038*
H10B	0.9506	0.6553	0.3568	0.038*
H10A	1.0053	0.5496	0.3441	0.038*
C11	0.6263 (3)	0.36275 (18)	0.49971 (16)	0.0267 (6)
H11A	0.5805	0.3094	0.5225	0.027*
H11B	0.5905	0.4238	0.5163	0.027*
H11C	0.7253	0.3594	0.5287	0.027*
C12	0.4431 (3)	0.35778 (17)	0.34699 (16)	0.0213 (5)
H12B	0.4009	0.3028	0.3715	0.021*
H12A	0.4052	0.4174	0.3667	0.021*
C13	0.5987 (2)	0.35583 (16)	0.39150 (15)	0.0177 (5)
C14	0.4740 (3)	0.35449 (17)	0.10478 (16)	0.0253 (6)
H14	0.5460	0.3588	0.0745	0.025*
C15	0.3403 (3)	0.34549 (18)	0.05079 (18)	0.0332 (7)
H15	0.3206	0.3424	−0.0157	0.033*
C16	0.2350 (3)	0.34100 (19)	0.09531 (19)	0.0355 (7)
H16	0.1424	0.3349	0.0593	0.035*
C17	0.2649 (3)	0.34528 (18)	0.18914 (18)	0.0263 (6)
H17	0.1937	0.3430	0.2202	0.026*
C18	0.4028 (3)	0.35314 (16)	0.24126 (16)	0.0225 (5)

	U11	U22	U33	U12	U13	U23
Fe1	0.0160 (2)	0.02093 (18)	0.02094 (18)	0.00010 (16)	0.00769 (14)	0.00049 (15)
Cl1	0.0378 (4)	0.0372 (4)	0.0234 (3)	0.0015 (3)	0.0140 (3)	0.0002 (3)
Cl2	0.0185 (4)	0.0517 (4)	0.0342 (3)	0.0017 (3)	0.0038 (3)	0.0017 (3)
O1	0.0232 (11)	0.0157 (9)	0.0363 (10)	−0.0017 (7)	0.0145 (8)	0.0011 (7)
O2	0.0225 (11)	0.0166 (9)	0.0380 (10)	0.0018 (7)	0.0141 (8)	0.0010 (8)
N1	0.0174 (12)	0.0160 (10)	0.0184 (10)	0.0008 (8)	0.0048 (9)	−0.0005 (8)
N3	0.0167 (12)	0.0157 (10)	0.0215 (10)	−0.0015 (8)	0.0063 (9)	0.0002 (8)
N2	0.0259 (13)	0.0276 (12)	0.0242 (11)	0.0005 (10)	0.0076 (9)	−0.0008 (9)
C1	0.0208 (15)	0.0156 (12)	0.0207 (12)	0.0002 (10)	0.0045 (10)	−0.0012 (10)
C2	0.0315 (17)	0.0166 (13)	0.0353 (15)	−0.0001 (11)	0.0148 (12)	0.0009 (11)
C3	0.0171 (14)	0.0187 (12)	0.0166 (12)	−0.0017 (10)	0.0033 (10)	0.0024 (10)
C4	0.0181 (14)	0.0161 (12)	0.0158 (11)	0.0008 (10)	0.0033 (10)	−0.0013 (10)
C5	0.0275 (17)	0.0151 (13)	0.0398 (15)	−0.0049 (11)	0.0123 (13)	−0.0007 (11)
C6	0.0264 (16)	0.0152 (13)	0.0338 (14)	−0.0021 (11)	0.0118 (12)	0.0006 (11)
C7	0.0393 (19)	0.0257 (14)	0.0288 (14)	−0.0030 (13)	0.0112 (13)	−0.0042 (12)
C8	0.0264 (17)	0.0239 (14)	0.0455 (17)	0.0023 (12)	0.0033 (13)	−0.0018 (13)
C9	0.054 (2)	0.0259 (15)	0.0365 (16)	0.0012 (14)	0.0201 (15)	0.0082 (13)
C10	0.0278 (18)	0.0258 (15)	0.062 (2)	−0.0077 (13)	0.0142 (15)	−0.0048 (14)
C11	0.0331 (17)	0.0281 (15)	0.0203 (12)	0.0014 (12)	0.0098 (11)	0.0004 (11)
C12	0.0181 (14)	0.0210 (13)	0.0257 (13)	−0.0014 (10)	0.0076 (10)	0.0008 (11)
C13	0.0174 (13)	0.0191 (12)	0.0186 (11)	0.0002 (10)	0.0083 (10)	−0.0001 (10)
C14	0.0310 (16)	0.0229 (13)	0.0224 (13)	0.0020 (11)	0.0078 (11)	−0.0033 (11)
C15	0.052 (2)	0.0222 (13)	0.0200 (13)	0.0049 (14)	−0.0001 (12)	−0.0018 (12)
C16	0.0263 (16)	0.0253 (14)	0.0426 (16)	0.0021 (13)	−0.0124 (13)	−0.0020 (13)
C17	0.0216 (15)	0.0190 (13)	0.0386 (15)	0.0014 (11)	0.0082 (12)	−0.0056 (12)
C18	0.0235 (15)	0.0163 (12)	0.0268 (13)	0.0020 (11)	0.0052 (11)	−0.0004 (10)

Fe1—N1	2.0821 (19)	C7—H7B	0.9800
Fe1—N3	2.073 (2)	C7—H7C	0.9800
Fe1—Cl1	2.2633 (7)	C8—H8B	0.9800
Fe1—Cl2	2.2552 (9)	C8—H8A	0.9800
O1—C3	1.349 (3)	C8—H8C	0.9800
O1—C2	1.453 (3)	C9—H9B	0.9800
O2—C4	1.340 (3)	C9—H9C	0.9800
O2—C5	1.458 (3)	C9—H9A	0.9800
N1—C3	1.272 (3)	C10—H10C	0.9800
N1—C1	1.502 (3)	C10—H10B	0.9800
N3—C4	1.271 (3)	C10—H10A	0.9800
N3—C6	1.505 (3)	C11—C13	1.551 (3)
N2—C18	1.335 (3)	C11—H11A	0.9800
N2—C14	1.354 (3)	C11—H11B	0.9800
C1—C8	1.508 (4)	C11—H11C	0.9800
C1—C7	1.518 (3)	C12—C18	1.507 (3)
C1—C2	1.536 (3)	C12—C13	1.535 (3)
C2—H2A	0.9900	C12—H12B	0.9900
C2—H2B	0.9900	C12—H12A	0.9900
C3—C13	1.507 (3)	C14—C15	1.381 (4)
C4—C13	1.506 (3)	C14—H14	0.9500
C5—C6	1.530 (3)	C15—C16	1.392 (4)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—C17	1.339 (4)
C6—C9	1.515 (4)	C16—H16	0.9500
C6—C10	1.517 (4)	C17—C18	1.408 (4)
C7—H7A	0.9800	C17—H17	0.9500
N3—Fe1—N1	88.85 (7)	C1—C8—H8B	109.5
N3—Fe1—Cl2	113.73 (6)	C1—C8—H8A	109.5
N1—Fe1—Cl2	111.27 (6)	H8B—C8—H8A	109.5
N3—Fe1—Cl1	112.50 (6)	C1—C8—H8C	109.5
N1—Fe1—Cl1	114.32 (6)	H8B—C8—H8C	109.5
Cl2—Fe1—Cl1	113.81 (3)	H8A—C8—H8C	109.5
C3—O1—C2	106.19 (18)	C6—C9—H9B	109.5
C4—O2—C5	105.92 (18)	C6—C9—H9C	109.5
C3—N1—C1	107.81 (19)	H9B—C9—H9C	109.5
C3—N1—Fe1	126.70 (16)	C6—C9—H9A	109.5
C1—N1—Fe1	124.42 (15)	H9B—C9—H9A	109.5
C4—N3—C6	107.4 (2)	H9C—C9—H9A	109.5
C4—N3—Fe1	126.74 (16)	C6—C10—H10C	109.5
C6—N3—Fe1	124.51 (15)	C6—C10—H10B	109.5
C18—N2—C14	118.6 (2)	H10C—C10—H10B	109.5
N1—C1—C8	110.4 (2)	C6—C10—H10A	109.5
N1—C1—C7	107.91 (19)	H10C—C10—H10A	109.5
C8—C1—C7	112.1 (2)	H10B—C10—H10A	109.5
N1—C1—C2	101.83 (18)	C13—C11—H11A	109.5
C8—C1—C2	112.1 (2)	C13—C11—H11B	109.5
C7—C1—C2	111.9 (2)	H11A—C11—H11B	109.5
O1—C2—C1	104.33 (18)	C13—C11—H11C	109.5
O1—C2—H2A	110.9	H11A—C11—H11C	109.5
C1—C2—H2A	110.9	H11B—C11—H11C	109.5
O1—C2—H2B	110.9	C18—C12—C13	114.2 (2)
C1—C2—H2B	110.9	C18—C12—H12B	108.7
H2A—C2—H2B	108.9	C13—C12—H12B	108.7
N1—C3—O1	117.2 (2)	C18—C12—H12A	108.7
N1—C3—C13	130.4 (2)	C13—C12—H12A	108.7
O1—C3—C13	112.4 (2)	H12B—C12—H12A	107.6
N3—C4—O2	117.6 (2)	C4—C13—C3	114.71 (19)
N3—C4—C13	130.5 (2)	C4—C13—C12	110.27 (19)
O2—C4—C13	111.7 (2)	C3—C13—C12	110.26 (19)
O2—C5—C6	104.15 (18)	C4—C13—C11	106.07 (19)
O2—C5—H5A	110.9	C3—C13—C11	106.22 (19)
C6—C5—H5A	110.9	C12—C13—C11	109.02 (19)
O2—C5—H5B	110.9	N2—C14—C15	121.7 (2)
C6—C5—H5B	110.9	N2—C14—H14	119.2
H5A—C5—H5B	108.9	C15—C14—H14	119.2
N3—C6—C9	108.9 (2)	C14—C15—C16	119.0 (2)
N3—C6—C10	109.7 (2)	C14—C15—H15	120.5
C9—C6—C10	111.9 (2)	C16—C15—H15	120.5
N3—C6—C5	101.67 (19)	C17—C16—C15	119.7 (3)
C9—C6—C5	111.6 (2)	C17—C16—H16	120.2
C10—C6—C5	112.5 (2)	C15—C16—H16	120.2
C1—C7—H7A	109.5	C16—C17—C18	119.3 (3)
C1—C7—H7B	109.5	C16—C17—H17	120.3
H7A—C7—H7B	109.5	C18—C17—H17	120.3
C1—C7—H7C	109.5	N2—C18—C17	121.8 (2)
H7A—C7—H7C	109.5	N2—C18—C12	116.3 (2)
H7B—C7—H7C	109.5	C17—C18—C12	121.9 (2)
N3—Fe1—N1—C3	9.1 (2)	C4—N3—C6—C9	−105.0 (2)
Cl2—Fe1—N1—C3	124.2 (2)	Fe1—N3—C6—C9	62.7 (3)
Cl1—Fe1—N1—C3	−105.2 (2)	C4—N3—C6—C10	132.2 (2)
N3—Fe1—N1—C1	175.79 (18)	Fe1—N3—C6—C10	−60.1 (3)
Cl2—Fe1—N1—C1	−69.11 (18)	C4—N3—C6—C5	12.9 (3)
Cl1—Fe1—N1—C1	61.53 (18)	Fe1—N3—C6—C5	−179.43 (15)
N1—Fe1—N3—C4	−9.9 (2)	O2—C5—C6—N3	−17.1 (3)
Cl2—Fe1—N3—C4	−122.71 (19)	O2—C5—C6—C9	98.8 (2)
Cl1—Fe1—N3—C4	106.0 (2)	O2—C5—C6—C10	−134.4 (2)
N1—Fe1—N3—C6	−175.18 (19)	N3—C4—C13—C3	−13.5 (4)
Cl2—Fe1—N3—C6	72.03 (19)	O2—C4—C13—C3	171.6 (2)
Cl1—Fe1—N3—C6	−59.23 (19)	N3—C4—C13—C12	−138.7 (3)
C3—N1—C1—C8	−130.6 (2)	O2—C4—C13—C12	46.5 (2)
Fe1—N1—C1—C8	60.6 (2)	N3—C4—C13—C11	103.4 (3)
C3—N1—C1—C7	106.6 (2)	O2—C4—C13—C11	−71.4 (2)
Fe1—N1—C1—C7	−62.3 (2)	N1—C3—C13—C4	12.4 (4)
C3—N1—C1—C2	−11.4 (3)	O1—C3—C13—C4	−171.2 (2)
Fe1—N1—C1—C2	179.80 (15)	N1—C3—C13—C12	137.6 (3)
C3—O1—C2—C1	−14.9 (2)	O1—C3—C13—C12	−46.0 (2)
N1—C1—C2—O1	15.6 (2)	N1—C3—C13—C11	−104.4 (3)
C8—C1—C2—O1	133.6 (2)	O1—C3—C13—C11	72.0 (2)
C7—C1—C2—O1	−99.4 (2)	C18—C12—C13—C4	63.0 (2)
C1—N1—C3—O1	2.4 (3)	C18—C12—C13—C3	−64.7 (2)
Fe1—N1—C3—O1	170.87 (14)	C18—C12—C13—C11	179.02 (19)
C1—N1—C3—C13	178.6 (2)	C18—N2—C14—C15	−1.3 (4)
Fe1—N1—C3—C13	−12.9 (4)	N2—C14—C15—C16	1.2 (4)
C2—O1—C3—N1	8.5 (3)	C14—C15—C16—C17	−0.1 (4)
C2—O1—C3—C13	−168.4 (2)	C15—C16—C17—C18	−0.7 (4)
C6—N3—C4—O2	−3.3 (3)	C14—N2—C18—C17	0.4 (4)
Fe1—N3—C4—O2	−170.57 (15)	C14—N2—C18—C12	−179.3 (2)
C6—N3—C4—C13	−177.9 (2)	C16—C17—C18—N2	0.6 (4)
Fe1—N3—C4—C13	14.8 (4)	C16—C17—C18—C12	−179.7 (2)
C5—O2—C4—N3	−8.6 (3)	C13—C12—C18—N2	−6.2 (3)
C5—O2—C4—C13	166.98 (19)	C13—C12—C18—C17	174.1 (2)
C4—O2—C5—C6	16.0 (2)