Dicarbon­yl(η5-cyclo­penta­dien­yl)(2,3-di­bromo­propanamine-κN)iron(II) tetra­fluoridoborate

M'thiruaine, C.M.; Friedrich, H.B.; Changamu, E.O.; Fernandes, M.A.

doi:10.1107/S1600536812025925

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m932

https://doi.org/10.1107/S1600536812025925

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Dicarbonyl(η⁵-cyclopentadienyl)(2,3-dibromopropanamine-κN)iron(II) tetrafluoridoborate

Cyprian M. M'thiruaine,^a ^* Holger B. Friedrich,^a Evans O. Changamu ^b and Manuel A. Fernandes ^c

^aSchool of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa, ^bChemistry Department, Kenyatta University, PO Box 43844, Nairobi, Kenya, and ^cSchool of Chemistry, University of the Witwatersrand, PO Wits, 2050 Johannesburg, South Africa
^*Correspondence e-mail: friedric@ukzn.ac.za

(Received 5 June 2012; accepted 7 June 2012; online 16 June 2012)

The title compound, [Fe(η⁵-C₅H₅)(NH₂CH₂CHBrCH₂Br)(CO)₂](BF₄) contains an Fe^II cation with a three-legged piano-stool coordination. The NH₂CH₂CHBrCH₂Br ligand contains a chiral carbon atom. The Fe—N bond length is 2.011 (3) Å and the Fe—Cp centroid distance is 1.7189 (5) Å. In the crystal, the ions are linked via two N—H⋯F interactions and a weak N—H⋯Br interaction.

Related literature

For the synthesis of the title compound and our previous work in this area, see: M'thiruaine et al. (2012b ). For related amino complexes, see: M'thiruaine et al. (2011a ,b , 2012a ,b). For piano-stool bromoalkyl complex structures, see: Friedrich et al. (2001 , 2004 ). For some applications of halogenated compounds, see: Gerebtzoff et al. (2004 ); Butler & Sandy (2009 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₃H₇Br₂N)(CO)₂]·(BF₄)
M_r = 480.69
Monoclinic, P c
a = 12.9385 (4) Å
b = 6.7123 (2) Å
c = 13.2959 (4) Å
β = 138.664 (2)°
V = 762.65 (4) Å³
Z = 2
Mo Kα radiation
μ = 6.27 mm⁻¹
T = 173 K
0.54 × 0.48 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: integration (SADABS; Bruker, 2005 ) T_min = 0.133, T_max = 0.264
8733 measured reflections
2944 independent reflections
2751 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.076
S = 1.10
2944 reflections
190 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: (Flack, 1983 )
Flack parameter: −0.003 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F4	0.92	2.15	2.951 (4)	145
N1—H1A⋯Br1	0.92	2.79	3.238 (3)	111
N1—H1B⋯F1ⁱ	0.92	2.06	2.935 (4)	158
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 Farrugia (1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025925/fj2567sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025925/fj2567Isup2.hkl

checkCIF report

Comment top

Halogenated compounds are of particular importance in pharmaceuticals and agrochemicals (Butler and Sandy 2009). A significant number of drugs and drug candidates in clinical development have halogenated structures because halogenation enhances membrane binding and permeation of drugs to the target sites (Gerebtzoff et al., 2004). Thus, structural determination of halogenated molecules, particularly the chiral compounds, is warranted.

The title compound (I) has been previously reported by us as the product of the bromination of the allylamino compound [Cp(CO)₂Fe{NH₂CH₂CH=CH₂}]BF₄ (M'thiruaine et al., 2012b). However, its molecular structure has not been previously reported. The compound is an enantiomerically pure chiral compound that crystallizes as the (S) enantiomer only. The unit cell of the title compound consisted of two molecular cations and two counteranions. The molecular cation displays a piano-stool geometry around the Fe^II ion with cyclopentadienyl coordinated to the metal centre in a pentahapto fashion, thus occupying the apical position, while two carbonyl ligands and the 2,3-dibromopropyl-1-amino ligand occupy the basal positions (Fig.1). The 2,3-dibromopropyl-1-amino ligand is coordinated to iron via the amino group, with an Fe—N bond length of 2.011 Å. This is within the reported Fe—N bond length range (M'thiruaine et al., 2011a,b; M'thiruaine et al., 2012a). The two Br atoms on the dibromopropylamino chain are in anti stereochemistry with a torsion angle Br1—C9—C10—Br2 =173.08 (19)^°. The C—Br bond lengths are 1.942 (5) and 1.978 (4) Å, which are close to the 1.946 (17) and 1.971 (3) Å reported for [Cp(CO)₃W{(CH₂)₃Br}] (Friedrich et al., 2001) and Cp*(CO)₂Fe{(CH₂)₃Br}] (Friedrich et al., 2004), respectively. The molecules are linked by three hydrogen bonds namely N1—H1A—F4, N1—H1A—Br1 and N1—H1B—F1 (Table 1).

Related literature top

For the synthesis of the title compound and our previous work in this area, see: M'thiruaine et al. (2012b). For related amino complexes, see: M'thiruaine et al.(2011a,b, 2012a,b). For piano-stool bromoalkyl complex structures, see: Friedrich et al. (2001, 2004). For some applications of halogenated compounds, see: Gerebtzoff et al. (2004); Butler & Sandy (2009).

Experimental top

The title compound was prepared according to a reported procedure (M'thiruaine et al., 2012b) and crystals were grown by layering a concentrated solution of the compound in CH₂Cl₂ with Et₂O and the mixture was kept undisturbed in the dark for four days.

Structure description top

For the synthesis of the title compound and our previous work in this area, see: M'thiruaine et al. (2012b). For related amino complexes, see: M'thiruaine et al.(2011a,b, 2012a,b). For piano-stool bromoalkyl complex structures, see: Friedrich et al. (2001, 2004). For some applications of halogenated compounds, see: Gerebtzoff et al. (2004); Butler & Sandy (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 Farrugia (1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of the title complex with the atom labeling scheme. Ellipsoids are drawn at 50% probability level.

Dicarbonyl(η⁵-cyclopentadienyl)(2,3-dibromopropanamine- κN)iron(II) tetrafluoridoborate top

Crystal data top

[Fe(C₅H₅)(C₃H₇Br₂N)(CO)₂]·(BF₄)	F(000) = 464
M_r = 480.69	D_x = 2.093 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 5868 reflections
a = 12.9385 (4) Å	θ = 2.3–28.3°
b = 6.7123 (2) Å	µ = 6.27 mm⁻¹
c = 13.2959 (4) Å	T = 173 K
β = 138.664 (2)°	Prismic, brown
V = 762.65 (4) Å³	0.54 × 0.48 × 0.29 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2944 independent reflections
Radiation source: fine-focus sealed tube	2751 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 28.0°, θ_min = 2.4°
Absorption correction: integration (SADABS; Bruker, 2005)	h = −17→16
T_min = 0.133, T_max = 0.264	k = −8→8
8733 measured reflections	l = −13→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0492P)² + 0.1443P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2944 reflections	Δρ_max = 0.76 e Å⁻³
190 parameters	Δρ_min = −0.64 e Å⁻³
2 restraints	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.003 (9)

Crystal data top

[Fe(C₅H₅)(C₃H₇Br₂N)(CO)₂]·(BF₄)	V = 762.65 (4) Å³
M_r = 480.69	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 12.9385 (4) Å	µ = 6.27 mm⁻¹
b = 6.7123 (2) Å	T = 173 K
c = 13.2959 (4) Å	0.54 × 0.48 × 0.29 mm
β = 138.664 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2944 independent reflections
Absorption correction: integration (SADABS; Bruker, 2005)	2751 reflections with I > 2σ(I)
T_min = 0.133, T_max = 0.264	R_int = 0.036
8733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.76 e Å⁻³
S = 1.10	Δρ_min = −0.64 e Å⁻³
2944 reflections	Absolute structure: (Flack, 1983)
190 parameters	Absolute structure parameter: −0.003 (9)
2 restraints

Special details top

Experimental. Face indexed absorption corrections carried out with XPREP

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
C1	0.2328 (5)	0.2525 (6)	0.2879 (5)	0.0312 (9)
H1	0.3279	0.2486	0.3203	0.037*
C2	0.1334 (5)	0.4194 (7)	0.2262 (4)	0.0341 (9)
H2	0.1504	0.5480	0.2107	0.041*
C3	0.0032 (5)	0.3607 (7)	0.1912 (4)	0.0344 (9)
H3	−0.0821	0.4430	0.1482	0.041*
C4	0.0241 (5)	0.1576 (7)	0.2321 (5)	0.0315 (8)
H4	−0.0454	0.0791	0.2206	0.038*
C5	0.1659 (4)	0.0924 (6)	0.2929 (4)	0.0275 (7)
H5	0.2092	−0.0374	0.3309	0.033*
C6	0.2019 (4)	0.5752 (6)	0.4680 (5)	0.0273 (8)
C7	0.1693 (4)	0.2165 (6)	0.5155 (4)	0.0234 (7)
C8	0.5160 (4)	0.1184 (5)	0.6589 (4)	0.0242 (7)
H8A	0.4996	0.0650	0.5784	0.029*
H8B	0.4636	0.0271	0.6685	0.029*
C9	0.6893 (4)	0.1202 (7)	0.8079 (4)	0.0278 (8)
H9	0.7069	0.1777	0.8892	0.033*
C10	0.7653 (5)	−0.0805 (7)	0.8575 (5)	0.0372 (10)
H10A	0.8802	−0.0656	0.9474	0.045*
H10B	0.7421	−0.1421	0.7746	0.045*
N1	0.4412 (3)	0.3170 (5)	0.6112 (3)	0.0193 (6)
H1A	0.4852	0.3976	0.5951	0.023*
H1B	0.4658	0.3708	0.6908	0.023*
O1	0.1941 (5)	0.7331 (5)	0.4917 (5)	0.0451 (9)
O2	0.1334 (3)	0.1479 (5)	0.5640 (3)	0.0363 (7)
Fe1	0.20737 (5)	0.32704 (7)	0.42396 (5)	0.01774 (11)
Br1	0.79524 (5)	0.28916 (9)	0.78419 (5)	0.04641 (14)
Br2	0.68883 (6)	−0.25147 (7)	0.90878 (6)	0.04643 (14)
B1	0.5163 (5)	0.7167 (7)	0.4432 (5)	0.0256 (8)
F1	0.4496 (4)	0.5759 (4)	0.3313 (3)	0.0449 (6)
F2	0.4611 (3)	0.9035 (4)	0.3751 (3)	0.0465 (7)
F3	0.6762 (3)	0.7131 (5)	0.5531 (4)	0.0514 (7)
F4	0.4694 (3)	0.6791 (4)	0.5072 (3)	0.0390 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0288 (19)	0.051 (3)	0.0181 (17)	−0.0010 (17)	0.0188 (16)	−0.0024 (16)
C2	0.036 (2)	0.042 (2)	0.0227 (19)	0.0036 (17)	0.0213 (18)	0.0101 (16)
C3	0.0237 (18)	0.047 (3)	0.0176 (17)	0.0083 (18)	0.0110 (15)	0.0071 (18)
C4	0.0272 (18)	0.036 (2)	0.0233 (18)	−0.0081 (16)	0.0166 (16)	−0.0079 (16)
C5	0.0300 (17)	0.0252 (18)	0.0212 (17)	−0.0020 (15)	0.0174 (15)	−0.0047 (14)
C6	0.0273 (17)	0.0250 (19)	0.0333 (19)	0.0037 (15)	0.0239 (16)	0.0025 (16)
C7	0.0203 (16)	0.0263 (17)	0.0195 (17)	−0.0052 (14)	0.0138 (16)	−0.0037 (14)
C8	0.0209 (16)	0.0234 (18)	0.0207 (16)	0.0011 (14)	0.0134 (15)	0.0019 (15)
C9	0.0226 (17)	0.039 (2)	0.0222 (17)	0.0034 (16)	0.0171 (16)	−0.0009 (17)
C10	0.0245 (18)	0.057 (3)	0.0250 (19)	0.0150 (19)	0.0170 (17)	0.009 (2)
N1	0.0135 (12)	0.0198 (14)	0.0190 (14)	−0.0032 (10)	0.0106 (12)	−0.0026 (11)
O1	0.054 (2)	0.0288 (17)	0.062 (2)	0.0017 (14)	0.046 (2)	−0.0012 (15)
O2	0.0341 (15)	0.0485 (18)	0.0330 (15)	−0.0088 (13)	0.0272 (14)	0.0020 (13)
Fe1	0.0162 (2)	0.0201 (2)	0.0159 (2)	0.00138 (18)	0.01175 (18)	0.00273 (19)
Br1	0.0292 (2)	0.0668 (3)	0.0469 (3)	−0.0055 (2)	0.0296 (2)	0.0008 (3)
Br2	0.0550 (3)	0.0445 (3)	0.0469 (3)	0.0230 (2)	0.0404 (3)	0.0209 (2)
B1	0.0239 (19)	0.032 (2)	0.0242 (19)	0.0033 (16)	0.0190 (18)	0.0062 (17)
F1	0.0642 (17)	0.0442 (15)	0.0465 (15)	−0.0069 (14)	0.0474 (15)	−0.0093 (13)
F2	0.0506 (16)	0.0380 (15)	0.0519 (17)	0.0035 (13)	0.0387 (15)	0.0123 (13)
F3	0.0291 (13)	0.071 (2)	0.0494 (17)	0.0058 (13)	0.0282 (13)	0.0121 (15)
F4	0.0508 (16)	0.0424 (14)	0.0471 (15)	−0.0083 (12)	0.0436 (15)	−0.0048 (12)

Geometric parameters (Å, º) top

C1—C5	1.413 (6)	C7—Fe1	1.781 (4)
C1—C2	1.414 (6)	C8—N1	1.481 (5)
C1—Fe1	2.128 (4)	C8—C9	1.511 (5)
C1—H1	0.9500	C8—H8A	0.9900
C2—C3	1.426 (6)	C8—H8B	0.9900
C2—Fe1	2.107 (4)	C9—C10	1.497 (6)
C2—H2	0.9500	C9—Br1	1.978 (4)
C3—C4	1.417 (7)	C9—H9	1.0000
C3—Fe1	2.081 (4)	C10—Br2	1.942 (5)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.408 (6)	C10—H10B	0.9900
C4—Fe1	2.083 (4)	N1—Fe1	2.011 (3)
C4—H4	0.9500	N1—H1A	0.9200
C5—Fe1	2.098 (4)	N1—H1B	0.9200
C5—H5	0.9500	B1—F3	1.370 (5)
C6—O1	1.132 (5)	B1—F1	1.387 (5)
C6—Fe1	1.784 (4)	B1—F2	1.389 (5)
C7—O2	1.138 (5)	B1—F4	1.391 (5)

C5—C1—C2	107.9 (4)	C9—C10—H10A	109.6
C5—C1—Fe1	69.3 (2)	Br2—C10—H10A	109.6
C2—C1—Fe1	69.7 (2)	C9—C10—H10B	109.6
C5—C1—H1	126.0	Br2—C10—H10B	109.6
C2—C1—H1	126.0	H10A—C10—H10B	108.1
Fe1—C1—H1	126.5	C8—N1—Fe1	116.9 (2)
C1—C2—C3	107.9 (4)	C8—N1—H1A	108.1
C1—C2—Fe1	71.3 (2)	Fe1—N1—H1A	108.1
C3—C2—Fe1	69.1 (2)	C8—N1—H1B	108.1
C1—C2—H2	126.1	Fe1—N1—H1B	108.1
C3—C2—H2	126.1	H1A—N1—H1B	107.3
Fe1—C2—H2	125.1	C7—Fe1—C6	93.75 (18)
C4—C3—C2	107.6 (4)	C7—Fe1—N1	94.06 (15)
C4—C3—Fe1	70.2 (2)	C6—Fe1—N1	91.07 (15)
C2—C3—Fe1	71.1 (2)	C7—Fe1—C3	111.59 (17)
C4—C3—H3	126.2	C6—Fe1—C3	93.88 (19)
C2—C3—H3	126.2	N1—Fe1—C3	153.45 (15)
Fe1—C3—H3	124.2	C7—Fe1—C4	87.97 (17)
C5—C4—C3	108.1 (4)	C6—Fe1—C4	128.48 (17)
C5—C4—Fe1	70.9 (2)	N1—Fe1—C4	140.23 (15)
C3—C4—Fe1	70.0 (2)	C3—Fe1—C4	39.79 (19)
C5—C4—H4	126.0	C7—Fe1—C5	103.00 (16)
C3—C4—H4	126.0	C6—Fe1—C5	157.66 (17)
Fe1—C4—H4	124.7	N1—Fe1—C5	102.23 (14)
C4—C5—C1	108.5 (4)	C3—Fe1—C5	66.36 (17)
C4—C5—Fe1	69.8 (2)	C4—Fe1—C5	39.37 (16)
C1—C5—Fe1	71.6 (2)	C7—Fe1—C2	151.17 (16)
C4—C5—H5	125.8	C6—Fe1—C2	92.41 (19)
C1—C5—H5	125.8	N1—Fe1—C2	113.97 (14)
Fe1—C5—H5	124.5	C3—Fe1—C2	39.82 (16)
O1—C6—Fe1	178.0 (4)	C4—Fe1—C2	66.40 (17)
O2—C7—Fe1	174.9 (3)	C5—Fe1—C2	65.86 (17)
N1—C8—C9	113.8 (3)	C7—Fe1—C1	141.39 (18)
N1—C8—H8A	108.8	C6—Fe1—C1	124.63 (17)
C9—C8—H8A	108.8	N1—Fe1—C1	89.72 (14)
N1—C8—H8B	108.8	C3—Fe1—C1	66.12 (17)
C9—C8—H8B	108.8	C4—Fe1—C1	65.86 (16)
H8A—C8—H8B	107.7	C5—Fe1—C1	39.06 (16)
C10—C9—C8	114.1 (3)	C2—Fe1—C1	39.00 (17)
C10—C9—Br1	106.4 (5)	F3—B1—F1	110.9 (4)
C8—C9—Br1	108.7 (3)	F3—B1—F2	109.7 (4)
C10—C9—H9	109.2	F1—B1—F2	108.4 (3)
C8—C9—H9	109.2	F3—B1—F4	110.3 (4)
Br1—C9—H9	109.2	F1—B1—F4	109.1 (3)
C9—C10—Br2	110.3 (3)	F2—B1—F4	108.4 (3)

C5—C1—C2—C3	−0.7 (4)	C3—C4—Fe1—N1	−137.9 (3)
Fe1—C1—C2—C3	−59.7 (3)	C5—C4—Fe1—C3	118.4 (3)
C5—C1—C2—Fe1	59.0 (3)	C3—C4—Fe1—C5	−118.4 (3)
C1—C2—C3—C4	0.1 (5)	C5—C4—Fe1—C2	80.1 (3)
Fe1—C2—C3—C4	−61.0 (3)	C3—C4—Fe1—C2	−38.3 (2)
C1—C2—C3—Fe1	61.1 (3)	C5—C4—Fe1—C1	37.3 (2)
C2—C3—C4—C5	0.6 (5)	C3—C4—Fe1—C1	−81.1 (3)
Fe1—C3—C4—C5	−61.0 (3)	C4—C5—Fe1—C7	70.2 (3)
C2—C3—C4—Fe1	61.6 (3)	C1—C5—Fe1—C7	−171.2 (2)
C3—C4—C5—C1	−1.0 (5)	C4—C5—Fe1—C6	−67.4 (5)
Fe1—C4—C5—C1	−61.5 (3)	C1—C5—Fe1—C6	51.2 (5)
C3—C4—C5—Fe1	60.4 (3)	C4—C5—Fe1—N1	167.4 (2)
C2—C1—C5—C4	1.1 (4)	C1—C5—Fe1—N1	−74.0 (2)
Fe1—C1—C5—C4	60.3 (3)	C4—C5—Fe1—C3	−37.9 (3)
C2—C1—C5—Fe1	−59.2 (3)	C1—C5—Fe1—C3	80.7 (3)
N1—C8—C9—C10	179.4 (3)	C1—C5—Fe1—C4	118.6 (3)
N1—C8—C9—Br1	−62.1 (3)	C4—C5—Fe1—C2	−81.6 (3)
C8—C9—C10—Br2	−67.2 (4)	C1—C5—Fe1—C2	37.0 (2)
Br1—C9—C10—Br2	173.08 (19)	C4—C5—Fe1—C1	−118.6 (3)
C9—C8—N1—Fe1	−174.8 (2)	C1—C2—Fe1—C7	−109.4 (4)
C8—N1—Fe1—C7	72.1 (3)	C3—C2—Fe1—C7	9.1 (5)
C8—N1—Fe1—C6	166.0 (3)	C1—C2—Fe1—C6	148.4 (3)
C8—N1—Fe1—C3	−93.2 (4)	C3—C2—Fe1—C6	−93.2 (3)
C8—N1—Fe1—C4	−19.6 (4)	C1—C2—Fe1—N1	56.1 (3)
C8—N1—Fe1—C5	−32.1 (3)	C3—C2—Fe1—N1	174.6 (2)
C8—N1—Fe1—C2	−100.9 (3)	C1—C2—Fe1—C3	−118.5 (4)
C8—N1—Fe1—C1	−69.4 (3)	C1—C2—Fe1—C4	−80.2 (3)
C4—C3—Fe1—C7	−57.7 (3)	C3—C2—Fe1—C4	38.2 (3)
C2—C3—Fe1—C7	−175.3 (3)	C1—C2—Fe1—C5	−37.0 (2)
C4—C3—Fe1—C6	−153.3 (3)	C3—C2—Fe1—C5	81.5 (3)
C2—C3—Fe1—C6	89.1 (3)	C3—C2—Fe1—C1	118.5 (4)
C4—C3—Fe1—N1	106.5 (4)	C5—C1—Fe1—C7	13.8 (4)
C2—C3—Fe1—N1	−11.1 (5)	C2—C1—Fe1—C7	133.2 (3)
C2—C3—Fe1—C4	−117.6 (4)	C5—C1—Fe1—C6	−158.9 (2)
C4—C3—Fe1—C5	37.5 (2)	C2—C1—Fe1—C6	−39.5 (3)
C2—C3—Fe1—C5	−80.1 (3)	C5—C1—Fe1—N1	110.0 (2)
C4—C3—Fe1—C2	117.6 (4)	C2—C1—Fe1—N1	−130.6 (3)
C4—C3—Fe1—C1	80.4 (3)	C5—C1—Fe1—C3	−81.4 (3)
C2—C3—Fe1—C1	−37.2 (3)	C2—C1—Fe1—C3	38.0 (3)
C5—C4—Fe1—C7	−113.5 (3)	C5—C1—Fe1—C4	−37.6 (2)
C3—C4—Fe1—C7	128.2 (3)	C2—C1—Fe1—C4	81.7 (3)
C5—C4—Fe1—C6	153.4 (2)	C2—C1—Fe1—C5	119.4 (4)
C3—C4—Fe1—C6	35.0 (3)	C5—C1—Fe1—C2	−119.4 (4)
C5—C4—Fe1—N1	−19.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F4	0.92	2.15	2.951 (4)	145
N1—H1A···Br1	0.92	2.79	3.238 (3)	111
N1—H1B···F1ⁱ	0.92	2.06	2.935 (4)	158

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₃H₇Br₂N)(CO)₂]·(BF₄)
M_r	480.69
Crystal system, space group	Monoclinic, Pc
Temperature (K)	173
a, b, c (Å)	12.9385 (4), 6.7123 (2), 13.2959 (4)
β (°)	138.664 (2)
V (Å³)	762.65 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.27
Crystal size (mm)	0.54 × 0.48 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Integration (SADABS; Bruker, 2005)
T_min, T_max	0.133, 0.264
No. of measured, independent and observed [I > 2σ(I)] reflections	8733, 2944, 2751
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.076, 1.10
No. of reflections	2944
No. of parameters	190
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.64
Absolute structure	(Flack, 1983)
Absolute structure parameter	−0.003 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SAINT-Plus and XPREP (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F4	0.92	2.15	2.951 (4)	145
N1—H1A···Br1	0.92	2.79	3.238 (3)	111
N1—H1B···F1ⁱ	0.92	2.06	2.935 (4)	158

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

We thank the University of KwaZulu-Natal for facilities and financial support.

References

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