Chlorido(2-imino-methyl-3-fluoro-phenyl-κC,N)tris-(trimethyl-phos-phane-κP)iron.

The title compound, [Fe(C(7)H(5)FN)Cl(C(3)H(9)P)(3)], was obtained as a product of the reaction of [Fe(Me(3)P)(4)] with a molar equivalent of (2-chloro-6-fluoro-phen-yl)methanimine in diethyl ether. This compound is sensitive to air, and rapidly decomposes when exposed to air for a few minutes. The Fe atom has an octa-hedral coordination geometry in which the bidentate fluoro-phenyl methanimine ligand forms the equatorial plane with the Cl atom and one of the trimethyl-phosphane ligands. The other two trimethyl-phosphane ligands are located in the axial positions. In the crystal, an N-H⋯Cl hydrogen bond occurs.

Related literature

For related literature regarding C—Cl bond activation, see: Wang et al. (2007 ▶); Wang & Love (2008 ▶); Shi et al. (2009 ▶). Related crystal structures of iron compounds have not yet been reported in the literature. For substituted phenyl­methanimine coordinated dihydride complexes of osmium, see: Schloerer et al. (2006 ▶); Barea et al. (1998 ▶).

Experimental

Crystal data

[Fe(C7H5FN)Cl(C3H9P)3]

M = 441.64

Monoclinic,

a = 8.9879 (6) Å

b = 19.4457 (13) Å

c = 13.5438 (7) Å

β = 114.937 (3)°

V = 2146.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.06 mm−1

T = 298 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.816, T max = 0.858

12499 measured reflections

4859 independent reflections

4109 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.071

S = 1.04

4859 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015030/ez2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015030/ez2239Isup2.hkl

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

[Fe(C7H5FN)Cl(C3H9P)3]	F(000) = 928
Mr = 441.64	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 5013 reflections
a = 8.9879 (6) Å	θ = 2.5–27.5°
b = 19.4457 (13) Å	µ = 1.06 mm−1
c = 13.5438 (7) Å	T = 298 K
β = 114.937 (3)°	Block, red
V = 2146.4 (2) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	4859 independent reflections
Radiation source: fine-focus sealed tube	4109 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→11
Tmin = 0.816, Tmax = 0.858	k = −24→25
12499 measured reflections	l = −17→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.4204P] where P = (Fo2 + 2Fc2)/3
4859 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.23 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
Fe	0.02988 (3)	0.391645 (11)	0.325636 (18)	0.01883 (7)
P3	0.25510 (6)	0.35114 (2)	0.46464 (4)	0.02733 (11)
P2	0.14694 (5)	0.39138 (2)	0.20985 (4)	0.02377 (11)
P1	−0.19959 (5)	0.44130 (2)	0.20154 (4)	0.02855 (11)
C1	−0.0641 (2)	0.29926 (8)	0.29408 (13)	0.0239 (3)
C6	−0.1656 (2)	0.28469 (9)	0.34912 (13)	0.0249 (4)
C5	−0.2479 (2)	0.22233 (10)	0.33495 (15)	0.0311 (4)
C4	−0.2322 (2)	0.17074 (10)	0.27239 (15)	0.0377 (5)
H4	−0.2877	0.1293	0.2647	0.045*
C3	−0.1304 (3)	0.18198 (9)	0.22048 (15)	0.0372 (5)
H3	−0.1154	0.1472	0.1784	0.045*
C2	−0.0503 (2)	0.24454 (9)	0.23040 (15)	0.0319 (4)
H2	0.0153	0.2505	0.1933	0.038*
N1	−0.08235 (18)	0.39126 (7)	0.42146 (12)	0.0272 (3)
H1	−0.0735	0.4256	0.4636	0.033*
C7	−0.1695 (2)	0.33880 (9)	0.42040 (14)	0.0291 (4)
H7	−0.2296	0.3360	0.4618	0.035*
C12	0.2364 (2)	0.47338 (9)	0.19708 (15)	0.0320 (4)
H12A	0.3218	0.4860	0.2663	0.048*
H12B	0.1530	0.5082	0.1737	0.048*
H12C	0.2816	0.4690	0.1445	0.048*
C13	0.0237 (3)	0.37148 (12)	0.06515 (15)	0.0414 (5)
H13A	−0.0624	0.4048	0.0344	0.062*
H13B	−0.0233	0.3265	0.0587	0.062*
H13C	0.0925	0.3728	0.0269	0.062*
C11	0.3211 (2)	0.33487 (10)	0.22908 (17)	0.0375 (5)
H11A	0.3555	0.3428	0.1719	0.056*
H11B	0.2884	0.2877	0.2273	0.056*
H11C	0.4105	0.3445	0.2981	0.056*
C8	−0.1846 (3)	0.51567 (12)	0.1234 (2)	0.0500 (6)
H8A	−0.2926	0.5328	0.0792	0.075*
H8B	−0.1322	0.5022	0.0776	0.075*
H8C	−0.1211	0.5511	0.1725	0.075*
C10	−0.3503 (2)	0.38749 (12)	0.09655 (18)	0.0475 (6)
H10A	−0.3822	0.3504	0.1302	0.071*
H10B	−0.3030	0.3692	0.0504	0.071*
H10C	−0.4449	0.4146	0.0538	0.071*
C9	−0.3291 (3)	0.47893 (11)	0.2609 (2)	0.0479 (6)
H9A	−0.4121	0.5070	0.2075	0.072*
H9B	−0.2632	0.5067	0.3224	0.072*
H9C	−0.3803	0.4429	0.2840	0.072*
C14	0.4433 (2)	0.40139 (11)	0.50640 (17)	0.0441 (5)
H14A	0.5319	0.3771	0.5623	0.066*
H14B	0.4286	0.4451	0.5340	0.066*
H14C	0.4684	0.4084	0.4449	0.066*
C15	0.3272 (3)	0.26346 (10)	0.46240 (18)	0.0451 (5)
H15A	0.3641	0.2595	0.4057	0.068*
H15B	0.2391	0.2317	0.4491	0.068*
H15C	0.4163	0.2532	0.5313	0.068*
C16	0.2353 (3)	0.34609 (12)	0.59360 (16)	0.0458 (5)
H16A	0.3393	0.3340	0.6511	0.069*
H16B	0.1554	0.3117	0.5881	0.069*
H16C	0.2008	0.3899	0.6092	0.069*
F	−0.34624 (14)	0.21266 (6)	0.38775 (10)	0.0473 (3)
Cl1	0.11769 (5)	0.50640 (2)	0.39209 (4)	0.02803 (10)

	U11	U22	U33	U12	U13	U23
Fe	0.02089 (13)	0.01713 (12)	0.02020 (13)	−0.00157 (9)	0.01036 (10)	−0.00253 (9)
P3	0.0284 (2)	0.0237 (2)	0.0260 (2)	−0.00102 (18)	0.00766 (19)	0.00456 (18)
P2	0.0242 (2)	0.0271 (2)	0.0231 (2)	−0.00228 (18)	0.01291 (18)	−0.00302 (17)
P1	0.0204 (2)	0.0289 (2)	0.0338 (3)	0.00095 (18)	0.00892 (19)	0.00162 (19)
C1	0.0254 (8)	0.0222 (8)	0.0227 (8)	−0.0012 (7)	0.0089 (7)	−0.0011 (7)
C6	0.0263 (9)	0.0237 (8)	0.0238 (8)	−0.0022 (7)	0.0096 (7)	0.0012 (7)
C5	0.0281 (9)	0.0313 (10)	0.0288 (9)	−0.0073 (8)	0.0069 (8)	0.0074 (8)
C4	0.0423 (11)	0.0239 (9)	0.0336 (10)	−0.0110 (8)	0.0031 (9)	0.0016 (8)
C3	0.0509 (12)	0.0219 (9)	0.0315 (10)	−0.0031 (8)	0.0103 (9)	−0.0076 (8)
C2	0.0395 (10)	0.0256 (9)	0.0329 (10)	−0.0050 (8)	0.0175 (8)	−0.0085 (8)
N1	0.0347 (8)	0.0233 (7)	0.0299 (8)	−0.0039 (6)	0.0198 (7)	−0.0072 (6)
C7	0.0325 (10)	0.0324 (10)	0.0290 (9)	−0.0031 (8)	0.0194 (8)	−0.0001 (8)
C12	0.0320 (10)	0.0350 (10)	0.0337 (10)	−0.0038 (8)	0.0184 (8)	0.0030 (8)
C13	0.0455 (12)	0.0559 (13)	0.0254 (10)	−0.0109 (10)	0.0174 (9)	−0.0086 (9)
C11	0.0375 (11)	0.0365 (11)	0.0479 (12)	0.0022 (9)	0.0273 (10)	−0.0050 (9)
C8	0.0326 (11)	0.0499 (13)	0.0586 (14)	0.0082 (10)	0.0106 (10)	0.0259 (11)
C10	0.0277 (10)	0.0572 (14)	0.0437 (13)	−0.0041 (10)	0.0015 (9)	−0.0069 (10)
C9	0.0316 (11)	0.0448 (12)	0.0696 (16)	0.0098 (9)	0.0235 (11)	−0.0042 (11)
C14	0.0296 (10)	0.0465 (12)	0.0406 (12)	−0.0066 (9)	−0.0004 (9)	0.0105 (10)
C15	0.0475 (12)	0.0315 (11)	0.0546 (13)	0.0139 (9)	0.0197 (11)	0.0145 (10)
C16	0.0600 (14)	0.0450 (12)	0.0273 (10)	−0.0034 (11)	0.0135 (10)	0.0072 (9)
F	0.0466 (7)	0.0466 (7)	0.0524 (7)	−0.0150 (6)	0.0245 (6)	0.0088 (6)
Cl1	0.0366 (2)	0.01904 (19)	0.0327 (2)	−0.00468 (17)	0.01878 (19)	−0.00525 (17)

Fe—N1	1.9508 (14)	C7—H7	0.9300
Fe—C1	1.9544 (16)	C12—H12A	0.9600
Fe—P2	2.2265 (5)	C12—H12B	0.9600
Fe—P3	2.2470 (5)	C12—H12C	0.9600
Fe—P1	2.2556 (5)	C13—H13A	0.9600
Fe—Cl1	2.4111 (5)	C13—H13B	0.9600
P3—C14	1.825 (2)	C13—H13C	0.9600
P3—C15	1.829 (2)	C11—H11A	0.9600
P3—C16	1.832 (2)	C11—H11B	0.9600
P2—C12	1.8268 (18)	C11—H11C	0.9600
P2—C11	1.8393 (19)	C8—H8A	0.9600
P2—C13	1.8404 (19)	C8—H8B	0.9600
P1—C10	1.824 (2)	C8—H8C	0.9600
P1—C9	1.824 (2)	C10—H10A	0.9600
P1—C8	1.830 (2)	C10—H10B	0.9600
C1—C2	1.408 (2)	C10—H10C	0.9600
C1—C6	1.429 (2)	C9—H9A	0.9600
C6—C5	1.391 (2)	C9—H9B	0.9600
C6—C7	1.439 (2)	C9—H9C	0.9600
C5—C4	1.359 (3)	C14—H14A	0.9600
C5—F	1.364 (2)	C14—H14B	0.9600
C4—C3	1.386 (3)	C14—H14C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C3—C2	1.391 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C2—H2	0.9300	C16—H16A	0.9600
N1—C7	1.283 (2)	C16—H16B	0.9600
N1—H1	0.8600	C16—H16C	0.9600
N1—Fe—C1	81.08 (7)	C6—C7—H7	123.2
N1—Fe—P2	177.39 (5)	P2—C12—H12A	109.5
C1—Fe—P2	97.64 (5)	P2—C12—H12B	109.5
N1—Fe—P3	88.69 (5)	H12A—C12—H12B	109.5
C1—Fe—P3	90.84 (5)	P2—C12—H12C	109.5
P2—Fe—P3	93.61 (2)	H12A—C12—H12C	109.5
N1—Fe—P1	86.02 (5)	H12B—C12—H12C	109.5
C1—Fe—P1	93.18 (5)	P2—C13—H13A	109.5
P2—Fe—P1	91.794 (19)	P2—C13—H13B	109.5
P3—Fe—P1	172.79 (2)	H13A—C13—H13B	109.5
N1—Fe—Cl1	86.27 (4)	P2—C13—H13C	109.5
C1—Fe—Cl1	167.34 (5)	H13A—C13—H13C	109.5
P2—Fe—Cl1	95.022 (17)	H13B—C13—H13C	109.5
P3—Fe—Cl1	88.522 (18)	P2—C11—H11A	109.5
P1—Fe—Cl1	86.246 (18)	P2—C11—H11B	109.5
C14—P3—C15	102.46 (10)	H11A—C11—H11B	109.5
C14—P3—C16	100.56 (11)	P2—C11—H11C	109.5
C15—P3—C16	98.25 (10)	H11A—C11—H11C	109.5
C14—P3—Fe	117.51 (7)	H11B—C11—H11C	109.5
C15—P3—Fe	120.89 (7)	P1—C8—H8A	109.5
C16—P3—Fe	113.72 (8)	P1—C8—H8B	109.5
C12—P2—C11	98.76 (9)	H8A—C8—H8B	109.5
C12—P2—C13	100.02 (9)	P1—C8—H8C	109.5
C11—P2—C13	96.86 (10)	H8A—C8—H8C	109.5
C12—P2—Fe	114.99 (6)	H8B—C8—H8C	109.5
C11—P2—Fe	121.91 (7)	P1—C10—H10A	109.5
C13—P2—Fe	119.97 (7)	P1—C10—H10B	109.5
C10—P1—C9	99.88 (11)	H10A—C10—H10B	109.5
C10—P1—C8	102.37 (11)	P1—C10—H10C	109.5
C9—P1—C8	98.87 (11)	H10A—C10—H10C	109.5
C10—P1—Fe	118.72 (8)	H10B—C10—H10C	109.5
C9—P1—Fe	113.34 (8)	P1—C9—H9A	109.5
C8—P1—Fe	120.13 (7)	P1—C9—H9B	109.5
C2—C1—C6	114.22 (15)	H9A—C9—H9B	109.5
C2—C1—Fe	133.41 (14)	P1—C9—H9C	109.5
C6—C1—Fe	112.36 (12)	H9A—C9—H9C	109.5
C5—C6—C1	121.36 (16)	H9B—C9—H9C	109.5
C5—C6—C7	124.61 (16)	P3—C14—H14A	109.5
C1—C6—C7	114.01 (15)	P3—C14—H14B	109.5
C4—C5—F	119.09 (16)	H14A—C14—H14B	109.5
C4—C5—C6	122.71 (18)	P3—C14—H14C	109.5
F—C5—C6	118.19 (17)	H14A—C14—H14C	109.5
C5—C4—C3	117.68 (17)	H14B—C14—H14C	109.5
C5—C4—H4	121.2	P3—C15—H15A	109.5
C3—C4—H4	121.2	P3—C15—H15B	109.5
C4—C3—C2	120.94 (18)	H15A—C15—H15B	109.5
C4—C3—H3	119.5	P3—C15—H15C	109.5
C2—C3—H3	119.5	H15A—C15—H15C	109.5
C3—C2—C1	123.01 (18)	H15B—C15—H15C	109.5
C3—C2—H2	118.5	P3—C16—H16A	109.5
C1—C2—H2	118.5	P3—C16—H16B	109.5
C7—N1—Fe	118.71 (12)	H16A—C16—H16B	109.5
C7—N1—H1	120.6	P3—C16—H16C	109.5
Fe—N1—H1	120.6	H16A—C16—H16C	109.5
N1—C7—C6	113.67 (15)	H16B—C16—H16C	109.5
N1—C7—H7	123.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.86	2.53	3.3339 (15)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.86	2.53	3.3339 (15)	157

Symmetry code: (i) .