{2-[2,2-Bis(4,4-dimethyl-4,5-di­hydro-1,3-oxazol-2-yl-κN)prop­yl]pyridine}­dichlorido­iron(II)

Roviello, G.; Tuzi, A.; Capacchione, C.; Milione, S.; Ferone, C.

doi:10.1107/S1600536813018047

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages m433-m434

doi:10.1107/S1600536813018047

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{2-[2,2-Bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl-κN)propyl]pyridine}dichloridoiron(II)

Giuseppina Roviello,^a ^* Angela Tuzi,^b Carmine Capacchione,^c Stefano Milione ^c and Claudio Ferone ^a

^aDipartimento di Ingegneria, Università di Napoli 'Parthenope', Centro Direzionale di Napoli, Isola C4, 80143 Napoli, Italy, ^bDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy, and ^cDipartimento di Chimica e Biologia, Università degli Studi di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano (Salerno), Italy
^*Correspondence e-mail: giuseppina.roviello@uniparthenope.it

(Received 25 June 2013; accepted 30 June 2013; online 6 July 2013)

The title compound,[FeCl₂(C₁₈H₂₅N₃O₂)], has a distorted tetrahedral 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-dihydro-1,3-oxazol-2-yl)propyl]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_r = 442.16
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.083
S = 1.01
4578 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018047/gg2121sup1.cif

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

checkCIF report

Comment top

Metal complexes containing bis(oxazoline) ligands have been widely investigated in the field of homogeneous and asymmetric catalysis. This type of ligands could stabilize the pseudotetrahedral coordination environment of iron(II) affording to efficient ATRP catalyst. The complex Fe(box-py)Cl₂ is analogous to Fe(box)Cl₂, described in the literature (Ferro et al., 2007) and has been investigated in order to obtaining an improved understanding of the factors influencing efficient ATRP catalysis in iron-based systems. The title compound Fe(box-py)Cl₂ (box-py = 2-[2,2-Bis-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-propyl]-pyridine), C₁₈H₂₅Cl₂Fe₁N₃O₂, has been used as catalyst in the framework of still not published studies on atom transfer radical polymerization (ATRP) of styrene and methylmethacrylate. The molecular structure of Fe(box-py)Cl₂ shows a distorted tetrahedral geometry, due to the constraints imposed by the ligand (N1—Fe1—N3 = 88.85 (7)°; Cl1—Fe1—Cl2 = 113.81 (3)°). The Fe—N and Fe—Cl bond distances are similar to that found for Fe(box)Cl₂ and for similar saliclylaldiminato complex (O`Reilly et al., 2003). Finally, the heteroaromatic ring is almost perpendicular to the six-membered chelated ring (angle between their mean planes is equal to 88.5 (1)°) and shows the nitrogen atom pointing towards the coordination environment of the iron.

Related literature top

For the analogous bis(oxazoline)iron(II) complex, see: Ferro et al. (2007). For ATRP active catalyst, 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 top

Fe(box-py)Cl₂ was obtained by the reaction of FeCl₂ with the ligand. Details for the synthesis will be reported in forthcoming work. Prismatic yellow crystals of the title complex were obtained by slow evaporation of a methylene chloride solution at room temperature.

Computing details top

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).

Figures top

Fig. 1. ORTEP view of the title compound. Thermal ellipsoids are drawn at 30% probability level.

{2-[2,2-Bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl-κN)propyl]pyridine}dichloridoiron(II) top

Crystal data top

[FeCl₂(C₁₈H₂₅N₃O₂)]	F(000) = 920
M_r = 442.16	D_x = 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

Data collection top

Bruker–Nonius KappaCCD diffractometer	4578 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
CCD rotation images, thick slices scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −17→17
T_min = 0.820, T_max = 0.903	l = −17→19
16483 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0268P)² + 1.0658P] where P = (F_o² + 2F_c²)/3
4578 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[FeCl₂(C₁₈H₂₅N₃O₂)]	V = 2003.5 (6) Å³
M_r = 442.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.102 (2) Å	µ = 1.04 mm⁻¹
b = 13.925 (3) Å	T = 173 K
c = 14.764 (2) Å	0.20 × 0.10 × 0.10 mm
β = 105.27 (1)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4578 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3033 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.903	R_int = 0.054
16483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
4578 reflections	Δρ_min = −0.30 e Å⁻³
240 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[FeCl₂(C₁₈H₂₅N₃O₂)]
M_r	442.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.102 (2), 13.925 (3), 14.764 (2)
β (°)	105.27 (1)
V (Å³)	2003.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.820, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	16483, 4578, 3033
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.083, 1.01
No. of reflections	4578
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico–Fisiche, Università degli Studi di Napoli "Federico II" for X-ray facilities.

References

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