1-(4-Bromo­phen­yl)ferrocene

Nyamori, V.O.; Bala, M.D.

doi:10.1107/S1600536808031759

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1376

doi:10.1107/S1600536808031759

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1-(4-Bromophenyl)ferrocene

Vincent O. Nyamori ^a and Muhammad D. Bala ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: bala@ukzn.ac.za

(Received 25 August 2008; accepted 1 October 2008; online 9 October 2008)

In the title compound, [Fe(C₅H₅)(C₁₁H₈Br)], the distance of the Fe atom from the centroids of the unsubstituted and substituted cyclopentadienyl (Cp) rings is 1.644 (1) and 1.643 (1) Å, respectively. The ferrocenyl moiety deviates from an eclipsed geometry, with marginally tilted Cp rings and an interplanar angle between the Cp and benzene rings of 13.0 (4)°. The crystal structure is stabilized by C—H⋯π interactions between a cyclopentadienyl H atom and the cyclopentadienyl ring of a neighbouring molecule.

Related literature

For related literature, see: Allen (2002 ); Anderson et al. (2003 ); Cambridge Crystallographic Data Centre (2002 ); Coe et al. (1994 ); Hor et al. (1991 ); Imrie et al. (2002 , 2003 ); Knoesen & Lotz (1999 ); Togni & Hayashi (1995 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₁H₈Br)]
M_r = 341.02
Monoclinic, P 2₁ /c
a = 16.4991 (3) Å
b = 9.9578 (2) Å
c = 7.9269 (1) Å
β = 97.084 (1)°
V = 1292.41 (4) Å³
Z = 4
Mo Kα radiation
μ = 4.24 mm⁻¹
T = 173 (2) K
0.37 × 0.32 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2005 ) T_min = 0.303, T_max = 0.756
15480 measured reflections
3126 independent reflections
2775 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 1.15
3126 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C5 cyclopentadienyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.95	2.90	3.780 (4)	154
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031759/lx2069sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031759/lx2069Isup2.hkl

checkCIF report

Comment top

Ferrocene compounds especially those synthesized by reacting a para-substituted phenylferrocene 4-Fc—C₆H₄-R (R = any atom or group) are of great interest in the field of material chemistry (Togni & Hayashi, 1995). They are employed as precursors in the synthesis of ferrocenomesogens with the ferrocenyl moiety incorporated as a terminal group (Imrie et al., 2002, 2003). Interest in these compounds stems from their potential use either as metathesis catalysts or therapeutic radiopharmaceuticals (Hor et al., 1991; Knoesen & Lotz, 1999). The compounds have also been used to synthesize non-linear optical materials containing molybdenum or tungsten redox centres (Coe et al.,1994).

In the title compound (I, Fig. 1), the distance of the Fe atom from the centroids of the unsubstituted (C1—C5) and the substituted (C6—C10) cyclopentadienyl rings are 1.644 (1) and 1.643 (1) Å respectively, indicating that the para- substitution (bromophenyl group) has little influence on Fe—Cp bonding interactions. The two Cp rings deviate from an eclipsed conformation with torsion angles around 11.0 (2)°. The rings are also marginally tilted towards each other with a tilt angle between the planes of the two rings of 0.83 (2)°. The interplanar angle between the Cp and the phenyl rings of (I) was 13.0 (4)°. This value is very close to the 12.8° observed by Anderson et al. (2003) as the median value upon analysis of 17 structures from the April 2002 version of the Cambridge Structural Database using ConQuest Version 1.4 (Allen, 2002). The molecular packing (Fig. 2) is stabilized by C—H···π interactions between a cyclopentadienyl H atom and the cyclopentadienyl ring of an adjacent molecule, with a C2—H2···Cgⁱ separation of 2.90 Å (Fig. 2 and Table 1; Cg is the centroid of the C1-C5 cyclopentadienyl ring, symmetry code as in Fig. 2).

Related literature top

For related literature, see: Allen (2002); Anderson et al. (2003); Cambridge Crystallographic Data Centre (2002); Coe et al. (1994); Hor et al. (1991); Imrie et al. (2002, 2003); Knoesen & Lotz (1999); Sheldrick (2008); Togni & Hayashi (1995).

Experimental top

The title compound (I) was synthesized via the diazonium reaction as follows: A solution of 4-bromobenzene diazonium sulfate was prepared by the reaction of 4-bromoaniline (20.02 g, 0.12 mol) in dilute sulfuric acid (100 cm³) to which sodium nitrite (11.65 g, 0.17 mol) was slowly added in water at 278 K. The reaction temperature was continually monitored and held at 278 K during the addition. The resultant solution was filtered and the filtrate was immediately added to a cold, well stirred solution of ferrocene(24.60 g, 0.13 mol) in diethyl ether (450 cm³). Stirring was continued at 278 K for 3 h and then at room temperature for a further 12 h. The ether layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel. Hexane was used to elute unreacted ferrocene and the product was eluted from the column using 1 : 1 hexane : dichloromethane mixture to yield 4.57 g, 11% of pure (I). mp 122–123 °C; Spectroscopic analysis: IR ν_max(KBr/cm^-1) 3086, 3053, 2925, 2853, 1588, 1509, 1446, 1406, 1383, 1278, 1103, 1088, 1066,1050, 1030, 1001, 884, 819; ¹H NMR (CDCl₃, 300 MHz) δ_H 7.41 (2H, d, J 8.5, ArH), 7.34 (2H, d, J 8.5, ArH), 4.62 (2H, t, J 1.8, C₅H₄),4.34 (2H, t, J 1.8, C₅H₄), 4.04 (5H, s, C₅H₅);

EI–MS 70 eV m/z 343 (18), 342 (96), 341 (22), 340 (M⁺, 100), 260 (3), 205 (23), 203 (10), 202 (9); Elemental analysis (Found: C, 56.4; H, 3.8%; M, 339.9551. required for C₁₆H₁₃FeBr: C, 56.6; H, 3.9%; M, 339.9550).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title complex with the atom labelling scheme. Ellipsoids are drawn at the 50% probability level.
	Fig. 2. A stereoview of the interactions in the crystal structure of (I). [Symmetry code: (i) x, -y+3/2, z-1/2; (ii) x, -y+3/2, z+1/2.]

1-(4-Bromophenyl)ferrocene top

Crystal data top

[Fe(C₅H₅)(C₁₁H₈Br)]	F(000) = 680
M_r = 341.02	D_x = 1.753 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 395–396 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.4991 (3) Å	Cell parameters from 8414 reflections
b = 9.9578 (2) Å	θ = 2.4–28.4°
c = 7.9269 (1) Å	µ = 4.24 mm⁻¹
β = 97.084 (1)°	T = 173 K
V = 1292.41 (4) Å³	Plate, orange
Z = 4	0.37 × 0.32 × 0.07 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3126 independent reflections
Radiation source: fine-focus sealed tube	2775 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.0°, θ_min = 1.2°
ϕ and ω scans	h = −21→21
Absorption correction: integration (XPREP; Bruker, 2005)	k = −13→13
T_min = 0.303, T_max = 0.756	l = −10→10
15480 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0124P)² + 2.8125P] where P = (F_o² + 2F_c²)/3
3126 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₁H₈Br)]	V = 1292.41 (4) Å³
M_r = 341.02	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.4991 (3) Å	µ = 4.24 mm⁻¹
b = 9.9578 (2) Å	T = 173 K
c = 7.9269 (1) Å	0.37 × 0.32 × 0.07 mm
β = 97.084 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3126 independent reflections
Absorption correction: integration (XPREP; Bruker, 2005)	2775 reflections with I > 2σ(I)
T_min = 0.303, T_max = 0.756	R_int = 0.039
15480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.15	Δρ_max = 0.53 e Å⁻³
3126 reflections	Δρ_min = −0.40 e Å⁻³
163 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br	−0.055964 (19)	0.43903 (4)	−0.29425 (5)	0.04324 (11)
Fe	0.35189 (2)	0.48664 (4)	0.27601 (5)	0.01850 (9)
C1	0.27574 (19)	0.6354 (3)	0.3370 (4)	0.0346 (7)
H1	0.2256	0.6612	0.2732	0.042*
C2	0.3538 (2)	0.6885 (3)	0.3185 (4)	0.0307 (7)
H2	0.3653	0.7560	0.2401	0.037*
C3	0.41137 (19)	0.6237 (3)	0.4365 (4)	0.0308 (6)
H3	0.4686	0.6397	0.4520	0.037*
C4	0.3689 (2)	0.5298 (3)	0.5287 (4)	0.0334 (7)
H4	0.3925	0.4720	0.6167	0.040*
C5	0.2854 (2)	0.5381 (3)	0.4659 (4)	0.0360 (7)
H5	0.2428	0.4865	0.5043	0.043*
C6	0.29438 (16)	0.3883 (3)	0.0676 (3)	0.0208 (5)
C7	0.36479 (16)	0.4587 (3)	0.0264 (3)	0.0225 (5)
H7	0.3652	0.5272	−0.0568	0.027*
C8	0.43450 (17)	0.4078 (3)	0.1324 (4)	0.0261 (6)
H8	0.4894	0.4363	0.1313	0.031*
C9	0.40733 (18)	0.3072 (3)	0.2393 (4)	0.0258 (6)
H9	0.4408	0.2569	0.3226	0.031*
C10	0.32169 (18)	0.2951 (3)	0.2001 (4)	0.0237 (6)
H10	0.2879	0.2350	0.2529	0.028*
C11	0.20996 (16)	0.4044 (3)	−0.0135 (3)	0.0213 (5)
C12	0.18754 (19)	0.5119 (3)	−0.1218 (4)	0.0309 (6)
H12	0.2269	0.5785	−0.1392	0.037*
C13	0.1081 (2)	0.5237 (3)	−0.2055 (4)	0.0340 (7)
H13	0.0933	0.5970	−0.2797	0.041*
C14	0.05166 (17)	0.4264 (3)	−0.1775 (4)	0.0295 (6)
C15	0.07133 (19)	0.3200 (3)	−0.0704 (4)	0.0337 (7)
H15	0.0314	0.2545	−0.0526	0.040*
C16	0.15020 (18)	0.3097 (3)	0.0114 (4)	0.0285 (6)
H16	0.1640	0.2364	0.0862	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.02264 (15)	0.0582 (2)	0.0466 (2)	0.00362 (14)	−0.00493 (13)	−0.00758 (17)
Fe	0.02091 (18)	0.01753 (18)	0.01723 (19)	−0.00139 (14)	0.00303 (14)	−0.00126 (14)
C1	0.0301 (15)	0.0309 (16)	0.0423 (19)	0.0082 (13)	0.0019 (13)	−0.0127 (14)
C2	0.0456 (18)	0.0172 (13)	0.0304 (16)	−0.0021 (12)	0.0082 (14)	−0.0022 (11)
C3	0.0297 (15)	0.0293 (15)	0.0330 (16)	−0.0040 (12)	0.0022 (12)	−0.0130 (12)
C4	0.054 (2)	0.0295 (15)	0.0171 (14)	0.0031 (14)	0.0049 (13)	−0.0048 (11)
C5	0.0425 (18)	0.0341 (17)	0.0358 (18)	−0.0090 (14)	0.0226 (14)	−0.0120 (14)
C6	0.0250 (13)	0.0199 (12)	0.0178 (13)	−0.0013 (10)	0.0036 (10)	−0.0017 (10)
C7	0.0237 (13)	0.0271 (14)	0.0174 (13)	−0.0009 (11)	0.0057 (10)	−0.0008 (10)
C8	0.0214 (13)	0.0325 (15)	0.0243 (14)	0.0014 (11)	0.0026 (11)	−0.0061 (11)
C9	0.0294 (14)	0.0239 (13)	0.0231 (14)	0.0055 (11)	−0.0015 (11)	−0.0036 (11)
C10	0.0313 (14)	0.0180 (12)	0.0217 (14)	−0.0025 (11)	0.0023 (11)	−0.0018 (10)
C11	0.0231 (13)	0.0225 (13)	0.0187 (13)	−0.0003 (10)	0.0037 (10)	−0.0032 (10)
C12	0.0292 (15)	0.0301 (15)	0.0325 (16)	−0.0060 (12)	−0.0003 (12)	0.0061 (12)
C13	0.0328 (16)	0.0331 (16)	0.0337 (17)	0.0012 (13)	−0.0051 (13)	0.0047 (13)
C14	0.0180 (12)	0.0402 (17)	0.0296 (16)	0.0027 (12)	0.0007 (11)	−0.0085 (13)
C15	0.0250 (14)	0.0360 (16)	0.0406 (18)	−0.0068 (13)	0.0061 (13)	−0.0038 (14)
C16	0.0275 (14)	0.0272 (14)	0.0307 (16)	−0.0028 (11)	0.0038 (12)	0.0026 (12)

Geometric parameters (Å, º) top

Br—C14	1.902 (3)	C6—C7	1.429 (4)
Fe—C3	2.033 (3)	C6—C10	1.432 (4)
Fe—C4	2.034 (3)	C6—C11	1.469 (4)
Fe—C5	2.035 (3)	C7—C8	1.431 (4)
Fe—C7	2.035 (3)	C7—H7	0.9500
Fe—C2	2.037 (3)	C8—C9	1.420 (4)
Fe—C8	2.038 (3)	C8—H8	0.9500
Fe—C1	2.039 (3)	C9—C10	1.414 (4)
Fe—C10	2.043 (3)	C9—H9	0.9500
Fe—C9	2.044 (3)	C10—H10	0.9500
Fe—C6	2.050 (3)	C11—C12	1.394 (4)
C1—C5	1.403 (5)	C11—C16	1.396 (4)
C1—C2	1.417 (4)	C12—C13	1.399 (4)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.405 (4)	C13—C14	1.381 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.424 (5)	C14—C15	1.371 (5)
C3—H3	0.9500	C15—C16	1.384 (4)
C4—C5	1.408 (5)	C15—H15	0.9500
C4—H4	0.9500	C16—H16	0.9500
C5—H5	0.9500

C3—Fe—C4	40.98 (13)	Fe—C3—H3	126.1
C3—Fe—C5	68.36 (13)	C5—C4—C3	107.6 (3)
C4—Fe—C5	40.50 (14)	C5—C4—Fe	69.79 (18)
C3—Fe—C7	126.85 (12)	C3—C4—Fe	69.49 (17)
C4—Fe—C7	165.51 (13)	C5—C4—H4	126.2
C5—Fe—C7	152.17 (14)	C3—C4—H4	126.2
C3—Fe—C2	40.37 (13)	Fe—C4—H4	126.1
C4—Fe—C2	68.37 (13)	C1—C5—C4	108.4 (3)
C5—Fe—C2	68.20 (13)	C1—C5—Fe	69.99 (17)
C7—Fe—C2	107.11 (12)	C4—C5—Fe	69.71 (17)
C3—Fe—C8	107.68 (12)	C1—C5—H5	125.8
C4—Fe—C8	127.68 (13)	C4—C5—H5	125.8
C5—Fe—C8	165.74 (14)	Fe—C5—H5	126.1
C7—Fe—C8	41.13 (11)	C7—C6—C10	107.1 (2)
C2—Fe—C8	118.32 (13)	C7—C6—C11	126.9 (2)
C3—Fe—C1	68.17 (13)	C10—C6—C11	126.0 (2)
C4—Fe—C1	68.10 (14)	C7—C6—Fe	68.97 (15)
C5—Fe—C1	40.30 (14)	C10—C6—Fe	69.28 (15)
C7—Fe—C1	118.13 (13)	C11—C6—Fe	128.33 (19)
C2—Fe—C1	40.69 (13)	C6—C7—C8	108.0 (2)
C8—Fe—C1	152.45 (14)	C6—C7—Fe	70.09 (15)
C3—Fe—C10	153.13 (12)	C8—C7—Fe	69.56 (16)
C4—Fe—C10	119.09 (12)	C6—C7—H7	126.0
C5—Fe—C10	108.57 (12)	C8—C7—H7	126.0
C7—Fe—C10	68.70 (11)	Fe—C7—H7	125.9
C2—Fe—C10	165.43 (12)	C9—C8—C7	108.1 (2)
C8—Fe—C10	68.36 (12)	C9—C8—Fe	69.89 (16)
C1—Fe—C10	127.81 (13)	C7—C8—Fe	69.32 (15)
C3—Fe—C9	119.06 (12)	C9—C8—H8	126.0
C4—Fe—C9	108.37 (12)	C7—C8—H8	126.0
C5—Fe—C9	128.08 (13)	Fe—C8—H8	126.4
C7—Fe—C9	68.88 (11)	C10—C9—C8	108.0 (2)
C2—Fe—C9	152.56 (13)	C10—C9—Fe	69.72 (16)
C8—Fe—C9	40.70 (12)	C8—C9—Fe	69.41 (16)
C1—Fe—C9	165.56 (13)	C10—C9—H9	126.0
C10—Fe—C9	40.48 (11)	C8—C9—H9	126.0
C3—Fe—C6	164.67 (12)	Fe—C9—H9	126.5
C4—Fe—C6	152.67 (12)	C9—C10—C6	108.7 (2)
C5—Fe—C6	118.56 (12)	C9—C10—Fe	69.81 (16)
C7—Fe—C6	40.94 (10)	C6—C10—Fe	69.77 (15)
C2—Fe—C6	126.92 (12)	C9—C10—H10	125.6
C8—Fe—C6	68.94 (11)	C6—C10—H10	125.6
C1—Fe—C6	107.50 (12)	Fe—C10—H10	126.4
C10—Fe—C6	40.95 (11)	C12—C11—C16	117.9 (3)
C9—Fe—C6	68.80 (11)	C12—C11—C6	121.3 (2)
C5—C1—C2	108.1 (3)	C16—C11—C6	120.8 (3)
C5—C1—Fe	69.70 (18)	C11—C12—C13	121.2 (3)
C2—C1—Fe	69.60 (17)	C11—C12—H12	119.4
C5—C1—H1	126.0	C13—C12—H12	119.4
C2—C1—H1	126.0	C14—C13—C12	118.4 (3)
Fe—C1—H1	126.3	C14—C13—H13	120.8
C3—C2—C1	107.9 (3)	C12—C13—H13	120.8
C3—C2—Fe	69.66 (17)	C15—C14—C13	121.9 (3)
C1—C2—Fe	69.71 (17)	C15—C14—Br	119.2 (2)
C3—C2—H2	126.0	C13—C14—Br	118.9 (2)
C1—C2—H2	126.0	C14—C15—C16	119.0 (3)
Fe—C2—H2	126.2	C14—C15—H15	120.5
C2—C3—C4	108.0 (3)	C16—C15—H15	120.5
C2—C3—Fe	69.96 (17)	C15—C16—C11	121.5 (3)
C4—C3—Fe	69.53 (17)	C15—C16—H16	119.2
C2—C3—H3	126.0	C11—C16—H16	119.2
C4—C3—H3	126.0

C3—Fe—C1—C5	−81.8 (2)	C9—Fe—C6—C10	37.07 (17)
C4—Fe—C1—C5	−37.5 (2)	C3—Fe—C6—C11	−79.1 (5)
C7—Fe—C1—C5	156.93 (19)	C4—Fe—C6—C11	68.0 (4)
C2—Fe—C1—C5	−119.4 (3)	C5—Fe—C6—C11	34.3 (3)
C8—Fe—C1—C5	−168.4 (2)	C7—Fe—C6—C11	−121.0 (3)
C10—Fe—C1—C5	73.0 (2)	C2—Fe—C6—C11	−48.8 (3)
C9—Fe—C1—C5	41.0 (6)	C8—Fe—C6—C11	−159.0 (3)
C6—Fe—C1—C5	113.8 (2)	C1—Fe—C6—C11	−8.0 (3)
C3—Fe—C1—C2	37.54 (19)	C10—Fe—C6—C11	120.1 (3)
C4—Fe—C1—C2	81.9 (2)	C9—Fe—C6—C11	157.2 (3)
C5—Fe—C1—C2	119.4 (3)	C10—C6—C7—C8	0.4 (3)
C7—Fe—C1—C2	−83.7 (2)	C11—C6—C7—C8	−177.7 (2)
C8—Fe—C1—C2	−49.0 (3)	Fe—C6—C7—C8	59.43 (19)
C10—Fe—C1—C2	−167.57 (17)	C10—C6—C7—Fe	−59.00 (18)
C9—Fe—C1—C2	160.4 (4)	C11—C6—C7—Fe	122.8 (3)
C6—Fe—C1—C2	−126.84 (18)	C3—Fe—C7—C6	−167.24 (17)
C5—C1—C2—C3	−0.1 (3)	C4—Fe—C7—C6	163.3 (4)
Fe—C1—C2—C3	−59.4 (2)	C5—Fe—C7—C6	−51.6 (3)
C5—C1—C2—Fe	59.3 (2)	C2—Fe—C7—C6	−127.18 (17)
C4—Fe—C2—C3	38.05 (19)	C8—Fe—C7—C6	119.1 (2)
C5—Fe—C2—C3	81.8 (2)	C1—Fe—C7—C6	−84.50 (19)
C7—Fe—C2—C3	−127.35 (18)	C10—Fe—C7—C6	38.03 (16)
C8—Fe—C2—C3	−84.2 (2)	C9—Fe—C7—C6	81.59 (17)
C1—Fe—C2—C3	119.2 (3)	C3—Fe—C7—C8	73.7 (2)
C10—Fe—C2—C3	161.7 (4)	C4—Fe—C7—C8	44.2 (5)
C9—Fe—C2—C3	−50.4 (3)	C5—Fe—C7—C8	−170.7 (2)
C6—Fe—C2—C3	−168.12 (17)	C2—Fe—C7—C8	113.71 (18)
C3—Fe—C2—C1	−119.2 (3)	C1—Fe—C7—C8	156.39 (18)
C4—Fe—C2—C1	−81.1 (2)	C10—Fe—C7—C8	−81.08 (18)
C5—Fe—C2—C1	−37.4 (2)	C9—Fe—C7—C8	−37.51 (17)
C7—Fe—C2—C1	113.5 (2)	C6—Fe—C7—C8	−119.1 (2)
C8—Fe—C2—C1	156.65 (19)	C6—C7—C8—C9	−0.4 (3)
C10—Fe—C2—C1	42.5 (5)	Fe—C7—C8—C9	59.35 (19)
C9—Fe—C2—C1	−169.5 (2)	C6—C7—C8—Fe	−59.76 (18)
C6—Fe—C2—C1	72.7 (2)	C3—Fe—C8—C9	114.28 (18)
C1—C2—C3—C4	0.0 (3)	C4—Fe—C8—C9	73.3 (2)
Fe—C2—C3—C4	−59.4 (2)	C5—Fe—C8—C9	42.8 (6)
C1—C2—C3—Fe	59.4 (2)	C7—Fe—C8—C9	−119.4 (2)
C4—Fe—C3—C2	−119.1 (3)	C2—Fe—C8—C9	156.84 (17)
C5—Fe—C3—C2	−81.4 (2)	C1—Fe—C8—C9	−169.2 (2)
C7—Fe—C3—C2	71.7 (2)	C10—Fe—C8—C9	−37.46 (16)
C8—Fe—C3—C2	113.20 (19)	C6—Fe—C8—C9	−81.58 (18)
C1—Fe—C3—C2	−37.82 (19)	C3—Fe—C8—C7	−126.30 (17)
C10—Fe—C3—C2	−169.9 (2)	C4—Fe—C8—C7	−167.27 (17)
C9—Fe—C3—C2	156.04 (18)	C5—Fe—C8—C7	162.2 (5)
C6—Fe—C3—C2	38.5 (5)	C2—Fe—C8—C7	−83.74 (19)
C5—Fe—C3—C4	37.7 (2)	C1—Fe—C8—C7	−49.8 (3)
C7—Fe—C3—C4	−169.18 (18)	C10—Fe—C8—C7	81.96 (17)
C2—Fe—C3—C4	119.1 (3)	C9—Fe—C8—C7	119.4 (2)
C8—Fe—C3—C4	−127.70 (19)	C6—Fe—C8—C7	37.84 (16)
C1—Fe—C3—C4	81.3 (2)	C7—C8—C9—C10	0.2 (3)
C10—Fe—C3—C4	−50.8 (3)	Fe—C8—C9—C10	59.22 (19)
C9—Fe—C3—C4	−84.9 (2)	C7—C8—C9—Fe	−59.00 (19)
C6—Fe—C3—C4	157.6 (4)	C3—Fe—C9—C10	157.07 (17)
C2—C3—C4—C5	0.0 (3)	C4—Fe—C9—C10	113.59 (18)
Fe—C3—C4—C5	−59.6 (2)	C5—Fe—C9—C10	72.8 (2)
C2—C3—C4—Fe	59.6 (2)	C7—Fe—C9—C10	−81.54 (17)
C3—Fe—C4—C5	118.8 (3)	C2—Fe—C9—C10	−168.1 (2)
C7—Fe—C4—C5	155.7 (4)	C8—Fe—C9—C10	−119.4 (2)
C2—Fe—C4—C5	81.3 (2)	C1—Fe—C9—C10	40.2 (6)
C8—Fe—C4—C5	−168.89 (19)	C6—Fe—C9—C10	−37.49 (16)
C1—Fe—C4—C5	37.35 (19)	C3—Fe—C9—C8	−83.5 (2)
C10—Fe—C4—C5	−84.8 (2)	C4—Fe—C9—C8	−126.99 (18)
C9—Fe—C4—C5	−127.73 (19)	C5—Fe—C9—C8	−167.72 (18)
C6—Fe—C4—C5	−48.5 (3)	C7—Fe—C9—C8	37.89 (16)
C5—Fe—C4—C3	−118.8 (3)	C2—Fe—C9—C8	−48.7 (3)
C7—Fe—C4—C3	36.9 (6)	C1—Fe—C9—C8	159.7 (5)
C2—Fe—C4—C3	−37.50 (18)	C10—Fe—C9—C8	119.4 (2)
C8—Fe—C4—C3	72.3 (2)	C6—Fe—C9—C8	81.94 (17)
C1—Fe—C4—C3	−81.5 (2)	C8—C9—C10—C6	0.0 (3)
C10—Fe—C4—C3	156.36 (18)	Fe—C9—C10—C6	59.08 (19)
C9—Fe—C4—C3	113.45 (19)	C8—C9—C10—Fe	−59.03 (19)
C6—Fe—C4—C3	−167.3 (2)	C7—C6—C10—C9	−0.3 (3)
C2—C1—C5—C4	0.1 (3)	C11—C6—C10—C9	177.9 (2)
Fe—C1—C5—C4	59.3 (2)	Fe—C6—C10—C9	−59.10 (19)
C2—C1—C5—Fe	−59.2 (2)	C7—C6—C10—Fe	58.80 (18)
C3—C4—C5—C1	−0.1 (3)	C11—C6—C10—Fe	−123.0 (3)
Fe—C4—C5—C1	−59.5 (2)	C3—Fe—C10—C9	−48.9 (3)
C3—C4—C5—Fe	59.4 (2)	C4—Fe—C10—C9	−84.5 (2)
C3—Fe—C5—C1	81.3 (2)	C5—Fe—C10—C9	−127.49 (19)
C4—Fe—C5—C1	119.5 (3)	C7—Fe—C10—C9	82.01 (18)
C7—Fe—C5—C1	−47.8 (3)	C2—Fe—C10—C9	157.9 (4)
C2—Fe—C5—C1	37.72 (19)	C8—Fe—C10—C9	37.67 (17)
C8—Fe—C5—C1	157.7 (5)	C1—Fe—C10—C9	−168.24 (18)
C10—Fe—C5—C1	−127.14 (19)	C6—Fe—C10—C9	120.0 (2)
C9—Fe—C5—C1	−168.01 (18)	C3—Fe—C10—C6	−168.9 (2)
C6—Fe—C5—C1	−83.5 (2)	C4—Fe—C10—C6	155.50 (17)
C3—Fe—C5—C4	−38.18 (19)	C5—Fe—C10—C6	112.47 (18)
C7—Fe—C5—C4	−167.3 (2)	C7—Fe—C10—C6	−38.02 (16)
C2—Fe—C5—C4	−81.8 (2)	C2—Fe—C10—C6	37.8 (5)
C8—Fe—C5—C4	38.2 (6)	C8—Fe—C10—C6	−82.37 (17)
C1—Fe—C5—C4	−119.5 (3)	C1—Fe—C10—C6	71.7 (2)
C10—Fe—C5—C4	113.35 (19)	C9—Fe—C10—C6	−120.0 (2)
C9—Fe—C5—C4	72.5 (2)	C7—C6—C11—C12	−12.5 (4)
C6—Fe—C5—C4	156.95 (18)	C10—C6—C11—C12	169.7 (3)
C3—Fe—C6—C7	42.0 (5)	Fe—C6—C11—C12	78.7 (3)
C4—Fe—C6—C7	−171.0 (2)	C7—C6—C11—C16	165.4 (3)
C5—Fe—C6—C7	155.38 (18)	C10—C6—C11—C16	−12.4 (4)
C2—Fe—C6—C7	72.3 (2)	Fe—C6—C11—C16	−103.4 (3)
C8—Fe—C6—C7	−38.01 (16)	C16—C11—C12—C13	−1.1 (5)
C1—Fe—C6—C7	113.01 (18)	C6—C11—C12—C13	176.9 (3)
C10—Fe—C6—C7	−118.9 (2)	C11—C12—C13—C14	0.4 (5)
C9—Fe—C6—C7	−81.79 (17)	C12—C13—C14—C15	0.3 (5)
C3—Fe—C6—C10	160.8 (4)	C12—C13—C14—Br	−178.6 (2)
C4—Fe—C6—C10	−52.1 (3)	C13—C14—C15—C16	−0.3 (5)
C5—Fe—C6—C10	−85.8 (2)	Br—C14—C15—C16	178.6 (2)
C7—Fe—C6—C10	118.9 (2)	C14—C15—C16—C11	−0.4 (5)
C2—Fe—C6—C10	−168.88 (17)	C12—C11—C16—C15	1.0 (4)
C8—Fe—C6—C10	80.85 (18)	C6—C11—C16—C15	−176.9 (3)
C1—Fe—C6—C10	−128.13 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.95	2.90	3.780 (4)	154

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₁H₈Br)]
M_r	341.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.4991 (3), 9.9578 (2), 7.9269 (1)
β (°)	97.084 (1)
V (Å³)	1292.41 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.24
Crystal size (mm)	0.37 × 0.32 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Integration (XPREP; Bruker, 2005)
T_min, T_max	0.303, 0.756
No. of measured, independent and observed [I > 2σ(I)] reflections	15480, 3126, 2775
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.15
No. of reflections	3126
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.40

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.95	2.90	3.780 (4)	153.9

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors thank Dr Manuel Fernandez for data collection, and the University of KwaZulu-Natal and the NRF for financial support.

References

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