1-(4-Bromo-phen-yl)ferrocene.

In the title compound, [Fe(C(5)H(5))(C(11)H(8)Br)], the distance of the Fe atom from the centroids of the unsubstituted and substituted cyclo-penta-dienyl (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 inter-planar angle between the Cp and benzene rings of 13.0 (4)°. The crystal structure is stabilized by C-H⋯π inter-actions between a cyclo-penta-dienyl H atom and the cyclo-penta-dienyl ring of a neighbouring mol-ecule.

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 = 341.02

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.075

S = 1.15

3126 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.40 e Å−3

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.

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

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

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

[Fe(C5H5)(C11H8Br)]	F(000) = 680
Mr = 341.02	Dx = 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

Bruker APEXII CCD area-detector diffractometer	3126 independent reflections
Radiation source: fine-focus sealed tube	2775 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 28.0°, θmin = 1.2°
φ and ω scans	h = −21→21
Absorption correction: integration (XPREP; Bruker, 2005)	k = −13→13
Tmin = 0.303, Tmax = 0.756	l = −10→10
15480 measured reflections

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(Fo2) + (0.0124P)2 + 2.8125P] where P = (Fo2 + 2Fc2)/3
3126 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .