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Acta Cryst. (2008). E64, m1376    [ doi:10.1107/S1600536808031759 ]

1-(4-Bromophenyl)ferrocene

V. O. Nyamori and M. D. Bala

Abstract top

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...[pi] interactions between a cyclopentadienyl H atom and the cyclopentadienyl ring of a neighbouring molecule.

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 νmax(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) δH 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).

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

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
[Figure 1] Fig. 1. Molecular structure of the title complex with the atom labelling scheme. Ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
Mr = 341.02Dx = 1.753 Mg m−3
Monoclinic, P21/cMelting point = 395–396 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.4991 (3) ÅCell parameters from 8414 reflections
b = 9.9578 (2) Åθ = 2.4–28.4°
c = 7.9269 (1) ŵ = 4.24 mm−1
β = 97.084 (1)°T = 173 K
V = 1292.41 (4) Å3Plate, orange
Z = 40.37 × 0.32 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3126 independent reflections
Radiation source: fine-focus sealed tube2775 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 10.0 pixels mm-1θmax = 28.0°, θmin = 1.2°
φ and ω scansh = −21→21
Absorption correction: integration
(XPREP; Bruker, 2005)		k = −13→13
Tmin = 0.303, Tmax = 0.756l = −10→10
15480 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0124P)2 + 2.8125P]
where P = (Fo2 + 2Fc2)/3
3126 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
[Fe(C5H5)(C11H8Br)]V = 1292.41 (4) Å3
Mr = 341.02Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.4991 (3) ŵ = 4.24 mm−1
b = 9.9578 (2) ÅT = 173 K
c = 7.9269 (1) Å0.37 × 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)
Tmin = 0.303, Tmax = 0.756Rint = 0.039
15480 measured reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.075Δρmax = 0.53 e Å−3
S = 1.15Δρmin = −0.40 e Å−3
3126 reflectionsAbsolute structure: ?
163 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Br−0.055964 (19)0.43903 (4)−0.29425 (5)0.04324 (11)
Fe0.35189 (2)0.48664 (4)0.27601 (5)0.01850 (9)
C10.27574 (19)0.6354 (3)0.3370 (4)0.0346 (7)
H10.22560.66120.27320.042*
C20.3538 (2)0.6885 (3)0.3185 (4)0.0307 (7)
H20.36530.75600.24010.037*
C30.41137 (19)0.6237 (3)0.4365 (4)0.0308 (6)
H30.46860.63970.45200.037*
C40.3689 (2)0.5298 (3)0.5287 (4)0.0334 (7)
H40.39250.47200.61670.040*
C50.2854 (2)0.5381 (3)0.4659 (4)0.0360 (7)
H50.24280.48650.50430.043*
C60.29438 (16)0.3883 (3)0.0676 (3)0.0208 (5)
C70.36479 (16)0.4587 (3)0.0264 (3)0.0225 (5)
H70.36520.5272−0.05680.027*
C80.43450 (17)0.4078 (3)0.1324 (4)0.0261 (6)
H80.48940.43630.13130.031*
C90.40733 (18)0.3072 (3)0.2393 (4)0.0258 (6)
H90.44080.25690.32260.031*
C100.32169 (18)0.2951 (3)0.2001 (4)0.0237 (6)
H100.28790.23500.25290.028*
C110.20996 (16)0.4044 (3)−0.0135 (3)0.0213 (5)
C120.18754 (19)0.5119 (3)−0.1218 (4)0.0309 (6)
H120.22690.5785−0.13920.037*
C130.1081 (2)0.5237 (3)−0.2055 (4)0.0340 (7)
H130.09330.5970−0.27970.041*
C140.05166 (17)0.4264 (3)−0.1775 (4)0.0295 (6)
C150.07133 (19)0.3200 (3)−0.0704 (4)0.0337 (7)
H150.03140.2545−0.05260.040*
C160.15020 (18)0.3097 (3)0.0114 (4)0.0285 (6)
H160.16400.23640.08620.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02264 (15)0.0582 (2)0.0466 (2)0.00362 (14)−0.00493 (13)−0.00758 (17)
Fe0.02091 (18)0.01753 (18)0.01723 (19)−0.00139 (14)0.00303 (14)−0.00126 (14)
C10.0301 (15)0.0309 (16)0.0423 (19)0.0082 (13)0.0019 (13)−0.0127 (14)
C20.0456 (18)0.0172 (13)0.0304 (16)−0.0021 (12)0.0082 (14)−0.0022 (11)
C30.0297 (15)0.0293 (15)0.0330 (16)−0.0040 (12)0.0022 (12)−0.0130 (12)
C40.054 (2)0.0295 (15)0.0171 (14)0.0031 (14)0.0049 (13)−0.0048 (11)
C50.0425 (18)0.0341 (17)0.0358 (18)−0.0090 (14)0.0226 (14)−0.0120 (14)
C60.0250 (13)0.0199 (12)0.0178 (13)−0.0013 (10)0.0036 (10)−0.0017 (10)
C70.0237 (13)0.0271 (14)0.0174 (13)−0.0009 (11)0.0057 (10)−0.0008 (10)
C80.0214 (13)0.0325 (15)0.0243 (14)0.0014 (11)0.0026 (11)−0.0061 (11)
C90.0294 (14)0.0239 (13)0.0231 (14)0.0055 (11)−0.0015 (11)−0.0036 (11)
C100.0313 (14)0.0180 (12)0.0217 (14)−0.0025 (11)0.0023 (11)−0.0018 (10)
C110.0231 (13)0.0225 (13)0.0187 (13)−0.0003 (10)0.0037 (10)−0.0032 (10)
C120.0292 (15)0.0301 (15)0.0325 (16)−0.0060 (12)−0.0003 (12)0.0061 (12)
C130.0328 (16)0.0331 (16)0.0337 (17)0.0012 (13)−0.0051 (13)0.0047 (13)
C140.0180 (12)0.0402 (17)0.0296 (16)0.0027 (12)0.0007 (11)−0.0085 (13)
C150.0250 (14)0.0360 (16)0.0406 (18)−0.0068 (13)0.0061 (13)−0.0038 (14)
C160.0275 (14)0.0272 (14)0.0307 (16)−0.0028 (11)0.0038 (12)0.0026 (12)
Geometric parameters (Å, °) top
Br—C141.902 (3)C6—C71.429 (4)
Fe—C32.033 (3)C6—C101.432 (4)
Fe—C42.034 (3)C6—C111.469 (4)
Fe—C52.035 (3)C7—C81.431 (4)
Fe—C72.035 (3)C7—H70.9500
Fe—C22.037 (3)C8—C91.420 (4)
Fe—C82.038 (3)C8—H80.9500
Fe—C12.039 (3)C9—C101.414 (4)
Fe—C102.043 (3)C9—H90.9500
Fe—C92.044 (3)C10—H100.9500
Fe—C62.050 (3)C11—C121.394 (4)
C1—C51.403 (5)C11—C161.396 (4)
C1—C21.417 (4)C12—C131.399 (4)
C1—H10.9500C12—H120.9500
C2—C31.405 (4)C13—C141.381 (4)
C2—H20.9500C13—H130.9500
C3—C41.424 (5)C14—C151.371 (5)
C3—H30.9500C15—C161.384 (4)
C4—C51.408 (5)C15—H150.9500
C4—H40.9500C16—H160.9500
C5—H50.9500
C3—Fe—C440.98 (13)Fe—C3—H3126.1
C3—Fe—C568.36 (13)C5—C4—C3107.6 (3)
C4—Fe—C540.50 (14)C5—C4—Fe69.79 (18)
C3—Fe—C7126.85 (12)C3—C4—Fe69.49 (17)
C4—Fe—C7165.51 (13)C5—C4—H4126.2
C5—Fe—C7152.17 (14)C3—C4—H4126.2
C3—Fe—C240.37 (13)Fe—C4—H4126.1
C4—Fe—C268.37 (13)C1—C5—C4108.4 (3)
C5—Fe—C268.20 (13)C1—C5—Fe69.99 (17)
C7—Fe—C2107.11 (12)C4—C5—Fe69.71 (17)
C3—Fe—C8107.68 (12)C1—C5—H5125.8
C4—Fe—C8127.68 (13)C4—C5—H5125.8
C5—Fe—C8165.74 (14)Fe—C5—H5126.1
C7—Fe—C841.13 (11)C7—C6—C10107.1 (2)
C2—Fe—C8118.32 (13)C7—C6—C11126.9 (2)
C3—Fe—C168.17 (13)C10—C6—C11126.0 (2)
C4—Fe—C168.10 (14)C7—C6—Fe68.97 (15)
C5—Fe—C140.30 (14)C10—C6—Fe69.28 (15)
C7—Fe—C1118.13 (13)C11—C6—Fe128.33 (19)
C2—Fe—C140.69 (13)C6—C7—C8108.0 (2)
C8—Fe—C1152.45 (14)C6—C7—Fe70.09 (15)
C3—Fe—C10153.13 (12)C8—C7—Fe69.56 (16)
C4—Fe—C10119.09 (12)C6—C7—H7126.0
C5—Fe—C10108.57 (12)C8—C7—H7126.0
C7—Fe—C1068.70 (11)Fe—C7—H7125.9
C2—Fe—C10165.43 (12)C9—C8—C7108.1 (2)
C8—Fe—C1068.36 (12)C9—C8—Fe69.89 (16)
C1—Fe—C10127.81 (13)C7—C8—Fe69.32 (15)
C3—Fe—C9119.06 (12)C9—C8—H8126.0
C4—Fe—C9108.37 (12)C7—C8—H8126.0
C5—Fe—C9128.08 (13)Fe—C8—H8126.4
C7—Fe—C968.88 (11)C10—C9—C8108.0 (2)
C2—Fe—C9152.56 (13)C10—C9—Fe69.72 (16)
C8—Fe—C940.70 (12)C8—C9—Fe69.41 (16)
C1—Fe—C9165.56 (13)C10—C9—H9126.0
C10—Fe—C940.48 (11)C8—C9—H9126.0
C3—Fe—C6164.67 (12)Fe—C9—H9126.5
C4—Fe—C6152.67 (12)C9—C10—C6108.7 (2)
C5—Fe—C6118.56 (12)C9—C10—Fe69.81 (16)
C7—Fe—C640.94 (10)C6—C10—Fe69.77 (15)
C2—Fe—C6126.92 (12)C9—C10—H10125.6
C8—Fe—C668.94 (11)C6—C10—H10125.6
C1—Fe—C6107.50 (12)Fe—C10—H10126.4
C10—Fe—C640.95 (11)C12—C11—C16117.9 (3)
C9—Fe—C668.80 (11)C12—C11—C6121.3 (2)
C5—C1—C2108.1 (3)C16—C11—C6120.8 (3)
C5—C1—Fe69.70 (18)C11—C12—C13121.2 (3)
C2—C1—Fe69.60 (17)C11—C12—H12119.4
C5—C1—H1126.0C13—C12—H12119.4
C2—C1—H1126.0C14—C13—C12118.4 (3)
Fe—C1—H1126.3C14—C13—H13120.8
C3—C2—C1107.9 (3)C12—C13—H13120.8
C3—C2—Fe69.66 (17)C15—C14—C13121.9 (3)
C1—C2—Fe69.71 (17)C15—C14—Br119.2 (2)
C3—C2—H2126.0C13—C14—Br118.9 (2)
C1—C2—H2126.0C14—C15—C16119.0 (3)
Fe—C2—H2126.2C14—C15—H15120.5
C2—C3—C4108.0 (3)C16—C15—H15120.5
C2—C3—Fe69.96 (17)C15—C16—C11121.5 (3)
C4—C3—Fe69.53 (17)C15—C16—H16119.2
C2—C3—H3126.0C11—C16—H16119.2
C4—C3—H3126.0
C3—Fe—C1—C5−81.8 (2)C9—Fe—C6—C1037.07 (17)
C4—Fe—C1—C5−37.5 (2)C3—Fe—C6—C11−79.1 (5)
C7—Fe—C1—C5156.93 (19)C4—Fe—C6—C1168.0 (4)
C2—Fe—C1—C5−119.4 (3)C5—Fe—C6—C1134.3 (3)
C8—Fe—C1—C5−168.4 (2)C7—Fe—C6—C11−121.0 (3)
C10—Fe—C1—C573.0 (2)C2—Fe—C6—C11−48.8 (3)
C9—Fe—C1—C541.0 (6)C8—Fe—C6—C11−159.0 (3)
C6—Fe—C1—C5113.8 (2)C1—Fe—C6—C11−8.0 (3)
C3—Fe—C1—C237.54 (19)C10—Fe—C6—C11120.1 (3)
C4—Fe—C1—C281.9 (2)C9—Fe—C6—C11157.2 (3)
C5—Fe—C1—C2119.4 (3)C10—C6—C7—C80.4 (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—C859.43 (19)
C10—Fe—C1—C2−167.57 (17)C10—C6—C7—Fe−59.00 (18)
C9—Fe—C1—C2160.4 (4)C11—C6—C7—Fe122.8 (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—C6163.3 (4)
Fe—C1—C2—C3−59.4 (2)C5—Fe—C7—C6−51.6 (3)
C5—C1—C2—Fe59.3 (2)C2—Fe—C7—C6−127.18 (17)
C4—Fe—C2—C338.05 (19)C8—Fe—C7—C6119.1 (2)
C5—Fe—C2—C381.8 (2)C1—Fe—C7—C6−84.50 (19)
C7—Fe—C2—C3−127.35 (18)C10—Fe—C7—C638.03 (16)
C8—Fe—C2—C3−84.2 (2)C9—Fe—C7—C681.59 (17)
C1—Fe—C2—C3119.2 (3)C3—Fe—C7—C873.7 (2)
C10—Fe—C2—C3161.7 (4)C4—Fe—C7—C844.2 (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—C8113.71 (18)
C3—Fe—C2—C1−119.2 (3)C1—Fe—C7—C8156.39 (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—C1113.5 (2)C6—Fe—C7—C8−119.1 (2)
C8—Fe—C2—C1156.65 (19)C6—C7—C8—C9−0.4 (3)
C10—Fe—C2—C142.5 (5)Fe—C7—C8—C959.35 (19)
C9—Fe—C2—C1−169.5 (2)C6—C7—C8—Fe−59.76 (18)
C6—Fe—C2—C172.7 (2)C3—Fe—C8—C9114.28 (18)
C1—C2—C3—C40.0 (3)C4—Fe—C8—C973.3 (2)
Fe—C2—C3—C4−59.4 (2)C5—Fe—C8—C942.8 (6)
C1—C2—C3—Fe59.4 (2)C7—Fe—C8—C9−119.4 (2)
C4—Fe—C3—C2−119.1 (3)C2—Fe—C8—C9156.84 (17)
C5—Fe—C3—C2−81.4 (2)C1—Fe—C8—C9−169.2 (2)
C7—Fe—C3—C271.7 (2)C10—Fe—C8—C9−37.46 (16)
C8—Fe—C3—C2113.20 (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—C2156.04 (18)C5—Fe—C8—C7162.2 (5)
C6—Fe—C3—C238.5 (5)C2—Fe—C8—C7−83.74 (19)
C5—Fe—C3—C437.7 (2)C1—Fe—C8—C7−49.8 (3)
C7—Fe—C3—C4−169.18 (18)C10—Fe—C8—C781.96 (17)
C2—Fe—C3—C4119.1 (3)C9—Fe—C8—C7119.4 (2)
C8—Fe—C3—C4−127.70 (19)C6—Fe—C8—C737.84 (16)
C1—Fe—C3—C481.3 (2)C7—C8—C9—C100.2 (3)
C10—Fe—C3—C4−50.8 (3)Fe—C8—C9—C1059.22 (19)
C9—Fe—C3—C4−84.9 (2)C7—C8—C9—Fe−59.00 (19)
C6—Fe—C3—C4157.6 (4)C3—Fe—C9—C10157.07 (17)
C2—C3—C4—C50.0 (3)C4—Fe—C9—C10113.59 (18)
Fe—C3—C4—C5−59.6 (2)C5—Fe—C9—C1072.8 (2)
C2—C3—C4—Fe59.6 (2)C7—Fe—C9—C10−81.54 (17)
C3—Fe—C4—C5118.8 (3)C2—Fe—C9—C10−168.1 (2)
C7—Fe—C4—C5155.7 (4)C8—Fe—C9—C10−119.4 (2)
C2—Fe—C4—C581.3 (2)C1—Fe—C9—C1040.2 (6)
C8—Fe—C4—C5−168.89 (19)C6—Fe—C9—C10−37.49 (16)
C1—Fe—C4—C537.35 (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—C837.89 (16)
C5—Fe—C4—C3−118.8 (3)C2—Fe—C9—C8−48.7 (3)
C7—Fe—C4—C336.9 (6)C1—Fe—C9—C8159.7 (5)
C2—Fe—C4—C3−37.50 (18)C10—Fe—C9—C8119.4 (2)
C8—Fe—C4—C372.3 (2)C6—Fe—C9—C881.94 (17)
C1—Fe—C4—C3−81.5 (2)C8—C9—C10—C60.0 (3)
C10—Fe—C4—C3156.36 (18)Fe—C9—C10—C659.08 (19)
C9—Fe—C4—C3113.45 (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—C40.1 (3)C11—C6—C10—C9177.9 (2)
Fe—C1—C5—C459.3 (2)Fe—C6—C10—C9−59.10 (19)
C2—C1—C5—Fe−59.2 (2)C7—C6—C10—Fe58.80 (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—Fe59.4 (2)C4—Fe—C10—C9−84.5 (2)
C3—Fe—C5—C181.3 (2)C5—Fe—C10—C9−127.49 (19)
C4—Fe—C5—C1119.5 (3)C7—Fe—C10—C982.01 (18)
C7—Fe—C5—C1−47.8 (3)C2—Fe—C10—C9157.9 (4)
C2—Fe—C5—C137.72 (19)C8—Fe—C10—C937.67 (17)
C8—Fe—C5—C1157.7 (5)C1—Fe—C10—C9−168.24 (18)
C10—Fe—C5—C1−127.14 (19)C6—Fe—C10—C9120.0 (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—C6155.50 (17)
C3—Fe—C5—C4−38.18 (19)C5—Fe—C10—C6112.47 (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—C637.8 (5)
C8—Fe—C5—C438.2 (6)C8—Fe—C10—C6−82.37 (17)
C1—Fe—C5—C4−119.5 (3)C1—Fe—C10—C671.7 (2)
C10—Fe—C5—C4113.35 (19)C9—Fe—C10—C6−120.0 (2)
C9—Fe—C5—C472.5 (2)C7—C6—C11—C12−12.5 (4)
C6—Fe—C5—C4156.95 (18)C10—C6—C11—C12169.7 (3)
C3—Fe—C6—C742.0 (5)Fe—C6—C11—C1278.7 (3)
C4—Fe—C6—C7−171.0 (2)C7—C6—C11—C16165.4 (3)
C5—Fe—C6—C7155.38 (18)C10—C6—C11—C16−12.4 (4)
C2—Fe—C6—C772.3 (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—C7113.01 (18)C6—C11—C12—C13176.9 (3)
C10—Fe—C6—C7−118.9 (2)C11—C12—C13—C140.4 (5)
C9—Fe—C6—C7−81.79 (17)C12—C13—C14—C150.3 (5)
C3—Fe—C6—C10160.8 (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—C16178.6 (2)
C7—Fe—C6—C10118.9 (2)C14—C15—C16—C11−0.4 (5)
C2—Fe—C6—C10−168.88 (17)C12—C11—C16—C151.0 (4)
C8—Fe—C6—C1080.85 (18)C6—C11—C16—C15−176.9 (3)
C1—Fe—C6—C10−128.13 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg1i0.952.903.780 (4)154
Symmetry codes: (i) x, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg1i0.952.903.780 (4)154
Symmetry codes: (i) x, −y+3/2, z−1/2.
Acknowledgements top

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

references
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