{(R,S(Fc),S(Fc))-2''-Bromo-2-[1-(dimethyl-amino)-ethyl-κN]-1,1''-biferrocene}trihydridoboron.

The title structure, [Fe(2)(C(5)H(5))(2)(C(14)H(19)BBrN)], contains a chiral and asymmetrically 2,2''-disubstituted biferrocene designed as precursor for enanti-oselective non-C(2)-symmetric biferrocenyldiphosphine catalysts. The mean bond lengths in the biferrocene unit are Fe-C = 2.048 (10) Å and C-C = 1.427 (8) Å within the cyclo-penta-dienyl rings. The B-N bond lengths of the BH(3) protected amine is 1.631 (3) Å. The inter-planar angle between the two connected cyclo-penta-dienyl rings is 54.29 (8)° and the corresponding Fe-Cg-Cg-Fe torsion angle is -52.5°. The conformation of the mol-ecule is stabilized by an intra-molecular C-H⋯Br inter-action.

Related literature

For general information on ferrocene-based diphosphines and their applications in asymmetric catalysis, see: Togni (1996 ▶); Blaser et al. (2007 ▶); Dai & Hou (2010 ▶). For the synthesis, coordination behavior and use in asymmetric catalysis of ligands based on biferrocenes, see: Sawamura et al. (1991 ▶); Nettekoven et al. (2000 ▶); Xiao et al. (2002 ▶); Espino et al. (2009 ▶); Kuwano (2010 ▶). For synthetic aspects of the title compound, see: Wang et al. (2011 ▶).

Experimental

Crystal data

[Fe2(C5H5)2(C14H19BBrN)]

M = 533.90

Orthorhombic,

a = 8.8791 (2) Å

b = 9.2210 (2) Å

c = 27.1292 (6) Å

V = 2221.18 (9) Å3

Z = 4

Mo Kα radiation

μ = 3.12 mm−1

T = 100 K

0.33 × 0.27 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.54, T max = 0.75

34891 measured reflections

6489 independent reflections

6288 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.054

S = 1.07

6489 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 2807 Friedel pairs

Flack parameter: 0.002 (5)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049270/bq2322sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049270/bq2322Isup2.hkl

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

[Fe2(C5H5)2(C14H19BBrN)]	F(000) = 1088
Mr = 533.90	Dx = 1.597 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9916 reflections
a = 8.8791 (2) Å	θ = 2.3–30.1°
b = 9.2210 (2) Å	µ = 3.12 mm−1
c = 27.1292 (6) Å	T = 100 K
V = 2221.18 (9) Å3	Prism, yellow
Z = 4	0.33 × 0.27 × 0.21 mm

Bruker Kappa APEXII CCD diffractometer	6489 independent reflections
Radiation source: fine-focus sealed tube	6288 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 30.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→11
Tmin = 0.54, Tmax = 0.75	k = −12→12
34891 measured reflections	l = −38→38

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)] = 0.023	H-atom parameters constrained
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.0234P)2 + 1.1731P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
6489 reflections	Δρmax = 0.69 e Å−3
266 parameters	Δρmin = −0.31 e Å−3
0 restraints	Absolute structure: Flack (1983), 2807 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.002 (5)

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
Br1	0.47251 (2)	0.185812 (19)	0.380922 (6)	0.01470 (4)
Fe1	0.30161 (3)	0.53063 (3)	0.298698 (9)	0.01275 (6)
Fe2	0.08967 (3)	0.22678 (3)	0.408373 (10)	0.01436 (6)
N1	0.57286 (19)	0.66124 (17)	0.43320 (6)	0.0148 (3)
B1	0.7399 (3)	0.6249 (3)	0.45489 (8)	0.0203 (4)
H1A	0.7446	0.6526	0.4897	0.030*
H1B	0.8157	0.6795	0.4363	0.030*
H1C	0.7598	0.5208	0.4517	0.030*
C1	0.2564 (2)	0.5202 (2)	0.37276 (6)	0.0123 (3)
C2	0.3899 (2)	0.60595 (19)	0.36404 (6)	0.0120 (3)
C3	0.3469 (2)	0.7240 (2)	0.33252 (7)	0.0162 (4)
H3	0.4123	0.7975	0.3205	0.019*
C4	0.1907 (3)	0.7127 (2)	0.32241 (7)	0.0199 (4)
H4	0.1337	0.7774	0.3026	0.024*
C5	0.1340 (2)	0.5881 (2)	0.34696 (7)	0.0176 (4)
H5	0.0326	0.5554	0.3464	0.021*
C6	0.2974 (2)	0.3255 (2)	0.27028 (7)	0.0178 (3)
H6	0.2661	0.2406	0.2873	0.021*
C7	0.4464 (2)	0.3820 (2)	0.26885 (6)	0.0159 (4)
H7	0.5320	0.3414	0.2847	0.019*
C8	0.4446 (2)	0.5103 (2)	0.23954 (7)	0.0180 (4)
H8	0.5288	0.5704	0.2325	0.022*
C9	0.2947 (3)	0.5326 (2)	0.22272 (7)	0.0227 (4)
H9	0.2612	0.6100	0.2024	0.027*
C10	0.2035 (3)	0.4183 (2)	0.24179 (7)	0.0224 (4)
H10	0.0985	0.4063	0.2364	0.027*
C11	0.2337 (2)	0.4012 (2)	0.40848 (7)	0.0125 (3)
C12	0.3112 (2)	0.2670 (2)	0.41713 (6)	0.0134 (3)
C13	0.2534 (2)	0.1987 (2)	0.46023 (7)	0.0180 (4)
H13	0.2861	0.1093	0.4739	0.022*
C14	0.1379 (2)	0.2896 (2)	0.47874 (7)	0.0198 (4)
H14	0.0789	0.2713	0.5073	0.024*
C15	0.1248 (2)	0.4126 (2)	0.44759 (7)	0.0180 (4)
H15	0.0554	0.4900	0.4519	0.022*
C16	−0.0151 (2)	0.2224 (2)	0.34155 (7)	0.0210 (4)
H16	0.0022	0.2875	0.3150	0.025*
C17	0.0622 (2)	0.0887 (2)	0.35010 (7)	0.0202 (4)
H17	0.1403	0.0495	0.3302	0.024*
C18	0.0020 (3)	0.0248 (2)	0.39343 (7)	0.0233 (4)
H18	0.0326	−0.0647	0.4076	0.028*
C19	−0.1121 (3)	0.1181 (2)	0.41198 (9)	0.0255 (4)
H19	−0.1709	0.1015	0.4407	0.031*
C20	−0.1235 (2)	0.2405 (2)	0.38022 (8)	0.0229 (4)
H20	−0.1907	0.3198	0.3840	0.028*
C21	0.5465 (2)	0.58227 (18)	0.38436 (6)	0.0122 (3)
H21	0.5562	0.4762	0.3913	0.015*
C22	0.6685 (2)	0.6203 (2)	0.34687 (7)	0.0192 (4)
H22A	0.6581	0.5578	0.3178	0.029*
H22B	0.7679	0.6055	0.3617	0.029*
H22C	0.6578	0.7220	0.3370	0.029*
C23	0.4604 (3)	0.6085 (2)	0.46983 (7)	0.0190 (4)
H23A	0.4772	0.6570	0.5015	0.029*
H23B	0.4714	0.5035	0.4741	0.029*
H23C	0.3586	0.6303	0.4580	0.029*
C24	0.5543 (3)	0.8216 (2)	0.42826 (8)	0.0235 (4)
H24A	0.4509	0.8435	0.4181	0.035*
H24B	0.6248	0.8583	0.4034	0.035*
H24C	0.5750	0.8681	0.4600	0.035*

	U11	U22	U33	U12	U13	U23
Br1	0.01301 (8)	0.01403 (7)	0.01707 (8)	0.00257 (7)	0.00186 (7)	0.00236 (6)
Fe1	0.01316 (13)	0.01367 (12)	0.01141 (11)	0.00278 (10)	−0.00227 (10)	0.00025 (9)
Fe2	0.01111 (13)	0.01697 (12)	0.01499 (12)	−0.00394 (10)	0.00234 (10)	−0.00310 (9)
N1	0.0172 (8)	0.0131 (7)	0.0141 (7)	−0.0022 (6)	−0.0019 (6)	−0.0017 (5)
B1	0.0170 (11)	0.0248 (11)	0.0191 (10)	−0.0028 (9)	−0.0051 (8)	−0.0003 (8)
C1	0.0099 (8)	0.0141 (8)	0.0129 (7)	0.0009 (6)	0.0002 (6)	−0.0022 (6)
C2	0.0117 (9)	0.0119 (7)	0.0124 (7)	0.0018 (6)	0.0002 (6)	−0.0024 (6)
C3	0.0192 (10)	0.0123 (8)	0.0171 (8)	0.0023 (7)	−0.0013 (7)	0.0010 (7)
C4	0.0207 (10)	0.0171 (9)	0.0219 (9)	0.0077 (8)	−0.0032 (8)	−0.0009 (7)
C5	0.0114 (9)	0.0200 (9)	0.0215 (9)	0.0053 (7)	−0.0011 (7)	−0.0026 (7)
C6	0.0195 (9)	0.0180 (8)	0.0159 (8)	−0.0017 (8)	0.0012 (7)	−0.0030 (7)
C7	0.0195 (11)	0.0152 (8)	0.0130 (7)	0.0032 (7)	0.0008 (6)	−0.0008 (6)
C8	0.0216 (11)	0.0180 (9)	0.0143 (8)	0.0009 (7)	0.0022 (7)	0.0013 (6)
C9	0.0277 (11)	0.0277 (10)	0.0129 (8)	0.0057 (9)	−0.0038 (8)	0.0020 (7)
C10	0.0208 (10)	0.0297 (11)	0.0167 (8)	0.0007 (9)	−0.0060 (8)	−0.0058 (8)
C11	0.0096 (8)	0.0156 (8)	0.0124 (7)	−0.0027 (6)	0.0005 (6)	−0.0028 (6)
C12	0.0120 (9)	0.0168 (8)	0.0115 (7)	−0.0035 (7)	0.0001 (6)	−0.0012 (6)
C13	0.0187 (10)	0.0215 (9)	0.0137 (7)	−0.0048 (8)	−0.0007 (6)	0.0024 (7)
C14	0.0167 (9)	0.0278 (11)	0.0149 (8)	−0.0087 (8)	0.0040 (7)	−0.0027 (7)
C15	0.0155 (10)	0.0231 (9)	0.0153 (8)	−0.0042 (7)	0.0035 (7)	−0.0060 (7)
C16	0.0174 (10)	0.0248 (9)	0.0207 (8)	−0.0060 (8)	−0.0014 (7)	−0.0052 (7)
C17	0.0190 (11)	0.0208 (9)	0.0209 (9)	−0.0056 (7)	0.0016 (7)	−0.0084 (7)
C18	0.0265 (12)	0.0200 (9)	0.0235 (9)	−0.0089 (8)	0.0011 (8)	−0.0031 (7)
C19	0.0180 (11)	0.0299 (11)	0.0285 (10)	−0.0116 (9)	0.0031 (8)	−0.0057 (9)
C20	0.0124 (9)	0.0283 (10)	0.0281 (10)	−0.0036 (7)	−0.0025 (8)	−0.0095 (9)
C21	0.0111 (8)	0.0127 (7)	0.0128 (7)	−0.0003 (6)	−0.0011 (6)	−0.0022 (6)
C22	0.0147 (10)	0.0272 (10)	0.0158 (8)	−0.0035 (8)	0.0026 (7)	0.0005 (7)
C23	0.0201 (10)	0.0230 (9)	0.0140 (8)	−0.0023 (8)	0.0036 (7)	−0.0044 (7)
C24	0.0306 (12)	0.0117 (8)	0.0283 (10)	0.0005 (8)	−0.0067 (8)	−0.0028 (7)

Br1—C12	1.8913 (19)	C6—C10	1.423 (3)
Fe1—C6	2.043 (2)	C6—H6	0.9500
Fe1—C3	2.046 (2)	C7—C8	1.426 (3)
Fe1—C7	2.046 (2)	C7—H7	0.9500
Fe1—C4	2.050 (2)	C8—C9	1.421 (3)
Fe1—C1	2.051 (2)	C8—H8	0.9500
Fe1—C5	2.052 (2)	C9—C10	1.426 (3)
Fe1—C10	2.053 (2)	C9—H9	0.9500
Fe1—C8	2.055 (2)	C10—H10	0.9500
Fe1—C2	2.059 (2)	C11—C12	1.435 (3)
Fe1—C9	2.062 (2)	C11—C15	1.440 (3)
Fe2—C12	2.015 (2)	C12—C13	1.424 (2)
Fe2—C16	2.038 (2)	C13—C14	1.417 (3)
Fe2—C13	2.040 (2)	C13—H13	0.9500
Fe2—C14	2.041 (2)	C14—C15	1.419 (3)
Fe2—C15	2.041 (2)	C14—H14	0.9500
Fe2—C17	2.044 (2)	C15—H15	0.9500
Fe2—C20	2.045 (2)	C16—C17	1.430 (3)
Fe2—C11	2.055 (2)	C16—C20	1.433 (3)
Fe2—C19	2.056 (2)	C16—H16	0.9500
Fe2—C18	2.059 (2)	C17—C18	1.419 (3)
N1—C23	1.490 (3)	C17—H17	0.9500
N1—C24	1.494 (3)	C18—C19	1.421 (3)
N1—C21	1.530 (2)	C18—H18	0.9500
N1—B1	1.631 (3)	C19—C20	1.424 (3)
B1—H1A	0.9800	C19—H19	0.9500
B1—H1B	0.9800	C20—H20	0.9500
B1—H1C	0.9800	C21—C22	1.527 (3)
C1—C5	1.437 (3)	C21—H21	1.0000
C1—C2	1.444 (3)	C22—H22A	0.9800
C1—C11	1.477 (3)	C22—H22B	0.9800
C2—C3	1.436 (2)	C22—H22C	0.9800
C2—C21	1.512 (3)	C23—H23A	0.9800
C3—C4	1.418 (3)	C23—H23B	0.9800
C3—H3	0.9500	C23—H23C	0.9800
C4—C5	1.420 (3)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800
C6—C7	1.422 (3)
C6—Fe1—C3	168.54 (8)	C3—C4—H4	125.8
C6—Fe1—C7	40.70 (8)	C5—C4—H4	125.8
C3—Fe1—C7	129.63 (8)	Fe1—C4—H4	126.4
C6—Fe1—C4	150.24 (9)	C4—C5—C1	108.25 (18)
C3—Fe1—C4	40.51 (8)	C4—C5—Fe1	69.66 (12)
C7—Fe1—C4	167.05 (8)	C1—C5—Fe1	69.48 (11)
C6—Fe1—C1	108.81 (7)	C4—C5—H5	125.9
C3—Fe1—C1	68.91 (7)	C1—C5—H5	125.9
C7—Fe1—C1	118.62 (7)	Fe1—C5—H5	126.6
C4—Fe1—C1	68.73 (8)	C7—C6—C10	108.03 (18)
C6—Fe1—C5	117.84 (8)	C7—C6—Fe1	69.75 (11)
C3—Fe1—C5	68.35 (8)	C10—C6—Fe1	70.03 (12)
C7—Fe1—C5	151.80 (8)	C7—C6—H6	126.0
C4—Fe1—C5	40.51 (8)	C10—C6—H6	126.0
C1—Fe1—C5	40.99 (8)	Fe1—C6—H6	125.8
C6—Fe1—C10	40.67 (8)	C6—C7—C8	107.99 (17)
C3—Fe1—C10	149.38 (8)	C6—C7—Fe1	69.55 (11)
C7—Fe1—C10	68.35 (9)	C8—C7—Fe1	69.99 (11)
C4—Fe1—C10	116.45 (9)	C6—C7—H7	126.0
C1—Fe1—C10	129.05 (8)	C8—C7—H7	126.0
C5—Fe1—C10	107.62 (9)	Fe1—C7—H7	126.0
C6—Fe1—C8	68.41 (8)	C9—C8—C7	108.04 (18)
C3—Fe1—C8	107.95 (8)	C9—C8—Fe1	70.08 (11)
C7—Fe1—C8	40.69 (7)	C7—C8—Fe1	69.32 (11)
C4—Fe1—C8	128.05 (8)	C9—C8—H8	126.0
C1—Fe1—C8	151.85 (8)	C7—C8—H8	126.0
C5—Fe1—C8	165.93 (8)	Fe1—C8—H8	126.2
C10—Fe1—C8	68.20 (9)	C8—C9—C10	107.95 (18)
C6—Fe1—C2	130.10 (7)	C8—C9—Fe1	69.53 (11)
C3—Fe1—C2	40.96 (7)	C10—C9—Fe1	69.37 (11)
C7—Fe1—C2	109.12 (7)	C8—C9—H9	126.0
C4—Fe1—C2	68.67 (8)	C10—C9—H9	126.0
C1—Fe1—C2	41.14 (7)	Fe1—C9—H9	126.6
C5—Fe1—C2	68.86 (8)	C6—C10—C9	108.0 (2)
C10—Fe1—C2	168.28 (8)	C6—C10—Fe1	69.30 (11)
C8—Fe1—C2	117.91 (8)	C9—C10—Fe1	70.07 (12)
C6—Fe1—C9	68.32 (8)	C6—C10—H10	126.0
C3—Fe1—C9	116.51 (8)	C9—C10—H10	126.0
C7—Fe1—C9	68.23 (8)	Fe1—C10—H10	126.2
C4—Fe1—C9	106.98 (8)	C12—C11—C15	105.34 (16)
C1—Fe1—C9	166.83 (9)	C12—C11—C1	133.01 (16)
C5—Fe1—C9	127.89 (9)	C15—C11—C1	121.38 (17)
C10—Fe1—C9	40.56 (9)	C12—C11—Fe2	67.89 (10)
C8—Fe1—C9	40.39 (9)	C15—C11—Fe2	68.91 (11)
C2—Fe1—C9	150.32 (9)	C1—C11—Fe2	131.69 (13)
C12—Fe2—C16	123.64 (8)	C13—C12—C11	110.07 (17)
C12—Fe2—C13	41.10 (7)	C13—C12—Br1	121.62 (15)
C16—Fe2—C13	159.46 (8)	C11—C12—Br1	128.27 (13)
C12—Fe2—C14	68.45 (8)	C13—C12—Fe2	70.36 (11)
C16—Fe2—C14	159.00 (9)	C11—C12—Fe2	70.83 (11)
C13—Fe2—C14	40.64 (8)	Br1—C12—Fe2	127.24 (9)
C12—Fe2—C15	68.59 (8)	C14—C13—C12	106.86 (18)
C16—Fe2—C15	123.37 (9)	C14—C13—Fe2	69.71 (11)
C13—Fe2—C15	68.79 (9)	C12—C13—Fe2	68.54 (11)
C14—Fe2—C15	40.69 (8)	C14—C13—H13	126.6
C12—Fe2—C17	108.80 (8)	C12—C13—H13	126.6
C16—Fe2—C17	41.00 (9)	Fe2—C13—H13	126.7
C13—Fe2—C17	122.65 (9)	C13—C14—C15	108.74 (17)
C14—Fe2—C17	157.73 (9)	C13—C14—Fe2	69.64 (11)
C15—Fe2—C17	160.77 (8)	C15—C14—Fe2	69.68 (11)
C12—Fe2—C20	159.37 (8)	C13—C14—H14	125.6
C16—Fe2—C20	41.10 (9)	C15—C14—H14	125.6
C13—Fe2—C20	157.70 (8)	Fe2—C14—H14	126.6
C14—Fe2—C20	121.74 (9)	C14—C15—C11	108.99 (18)
C15—Fe2—C20	106.51 (8)	C14—C15—Fe2	69.63 (11)
C17—Fe2—C20	68.84 (9)	C11—C15—Fe2	69.93 (10)
C12—Fe2—C11	41.28 (7)	C14—C15—H15	125.5
C16—Fe2—C11	107.51 (8)	C11—C15—H15	125.5
C13—Fe2—C11	69.80 (8)	Fe2—C15—H15	126.5
C14—Fe2—C11	69.25 (8)	C17—C16—C20	107.67 (18)
C15—Fe2—C11	41.15 (7)	C17—C16—Fe2	69.74 (11)
C17—Fe2—C11	124.25 (8)	C20—C16—Fe2	69.69 (11)
C20—Fe2—C11	121.89 (8)	C17—C16—H16	126.2
C12—Fe2—C19	159.19 (9)	C20—C16—H16	126.2
C16—Fe2—C19	68.58 (9)	Fe2—C16—H16	126.0
C13—Fe2—C19	121.78 (9)	C18—C17—C16	108.16 (19)
C14—Fe2—C19	106.07 (9)	C18—C17—Fe2	70.32 (11)
C15—Fe2—C19	121.18 (9)	C16—C17—Fe2	69.27 (11)
C17—Fe2—C19	68.22 (9)	C18—C17—H17	125.9
C20—Fe2—C19	40.63 (9)	C16—C17—H17	125.9
C11—Fe2—C19	157.55 (9)	Fe2—C17—H17	126.1
C12—Fe2—C18	123.97 (9)	C17—C18—C19	108.1 (2)
C16—Fe2—C18	68.54 (9)	C17—C18—Fe2	69.21 (11)
C13—Fe2—C18	106.89 (9)	C19—C18—Fe2	69.67 (12)
C14—Fe2—C18	121.37 (8)	C17—C18—H18	126.0
C15—Fe2—C18	156.91 (8)	C19—C18—H18	126.0
C17—Fe2—C18	40.47 (8)	Fe2—C18—H18	126.7
C20—Fe2—C18	68.42 (9)	C18—C19—C20	108.41 (19)
C11—Fe2—C18	160.67 (8)	C18—C19—Fe2	69.92 (12)
C19—Fe2—C18	40.41 (9)	C20—C19—Fe2	69.27 (12)
C23—N1—C24	107.98 (16)	C18—C19—H19	125.8
C23—N1—C21	108.64 (14)	C20—C19—H19	125.8
C24—N1—C21	112.12 (14)	Fe2—C19—H19	126.6
C23—N1—B1	107.57 (15)	C19—C20—C16	107.67 (19)
C24—N1—B1	109.64 (16)	C19—C20—Fe2	70.10 (13)
C21—N1—B1	110.73 (15)	C16—C20—Fe2	69.21 (11)
N1—B1—H1A	109.5	C19—C20—H20	126.2
N1—B1—H1B	109.5	C16—C20—H20	126.2
H1A—B1—H1B	109.5	Fe2—C20—H20	126.1
N1—B1—H1C	109.5	C2—C21—C22	112.12 (15)
H1A—B1—H1C	109.5	C2—C21—N1	112.82 (14)
H1B—B1—H1C	109.5	C22—C21—N1	111.04 (15)
C5—C1—C2	107.56 (16)	C2—C21—H21	106.8
C5—C1—C11	122.70 (17)	C22—C21—H21	106.8
C2—C1—C11	128.77 (16)	N1—C21—H21	106.8
C5—C1—Fe1	69.53 (11)	C21—C22—H22A	109.5
C2—C1—Fe1	69.71 (10)	C21—C22—H22B	109.5
C11—C1—Fe1	134.76 (13)	H22A—C22—H22B	109.5
C3—C2—C1	107.17 (16)	C21—C22—H22C	109.5
C3—C2—C21	124.81 (17)	H22A—C22—H22C	109.5
C1—C2—C21	128.00 (15)	H22B—C22—H22C	109.5
C3—C2—Fe1	69.03 (10)	N1—C23—H23A	109.5
C1—C2—Fe1	69.15 (10)	N1—C23—H23B	109.5
C21—C2—Fe1	127.99 (12)	H23A—C23—H23B	109.5
C4—C3—C2	108.60 (18)	N1—C23—H23C	109.5
C4—C3—Fe1	69.90 (11)	H23A—C23—H23C	109.5
C2—C3—Fe1	70.01 (10)	H23B—C23—H23C	109.5
C4—C3—H3	125.7	N1—C24—H24A	109.5
C2—C3—H3	125.7	N1—C24—H24B	109.5
Fe1—C3—H3	126.0	H24A—C24—H24B	109.5
C3—C4—C5	108.41 (17)	N1—C24—H24C	109.5
C3—C4—Fe1	69.59 (11)	H24A—C24—H24C	109.5
C5—C4—Fe1	69.82 (11)	H24B—C24—H24C	109.5
C5—C1—C2—C3	−0.7 (2)	Fe2—C11—C12—C13	−59.61 (13)
C11—C1—C2—C3	−169.48 (17)	C15—C11—C12—Br1	−178.14 (14)
C5—C1—C2—C21	177.98 (17)	C1—C11—C12—Br1	−4.3 (3)
C11—C1—C2—C21	9.2 (3)	Fe2—C11—C12—Br1	122.80 (15)
Fe1—C1—C2—C21	−122.56 (18)	C15—C11—C12—Fe2	59.06 (12)
C5—C1—C2—Fe1	−59.46 (12)	C1—C11—C12—Fe2	−127.1 (2)
C11—C1—C2—Fe1	131.75 (19)	C11—C12—C13—C14	0.5 (2)
C1—C2—C3—C4	0.6 (2)	Br1—C12—C13—C14	178.23 (13)
C21—C2—C3—C4	−178.11 (16)	Fe2—C12—C13—C14	−59.44 (13)
Fe1—C2—C3—C4	59.45 (13)	C11—C12—C13—Fe2	59.90 (13)
C1—C2—C3—Fe1	−58.84 (12)	Br1—C12—C13—Fe2	−122.33 (13)
C21—C2—C3—Fe1	122.43 (17)	C12—C13—C14—C15	−0.2 (2)
C2—C3—C4—C5	−0.3 (2)	Fe2—C13—C14—C15	−58.87 (14)
Fe1—C3—C4—C5	59.22 (14)	C12—C13—C14—Fe2	58.69 (13)
C2—C3—C4—Fe1	−59.52 (13)	C13—C14—C15—C11	−0.2 (2)
C3—C4—C5—C1	−0.1 (2)	Fe2—C14—C15—C11	−59.02 (13)
Fe1—C4—C5—C1	58.94 (13)	C13—C14—C15—Fe2	58.84 (14)
C3—C4—C5—Fe1	−59.08 (14)	C12—C11—C15—C14	0.4 (2)
C2—C1—C5—C4	0.5 (2)	C1—C11—C15—C14	−174.31 (16)
C11—C1—C5—C4	170.14 (16)	Fe2—C11—C15—C14	58.83 (14)
Fe1—C1—C5—C4	−59.06 (13)	C12—C11—C15—Fe2	−58.39 (12)
C2—C1—C5—Fe1	59.57 (12)	C1—C11—C15—Fe2	126.86 (17)
C11—C1—C5—Fe1	−130.80 (17)	C20—C16—C17—C18	0.2 (2)
C10—C6—C7—C8	0.2 (2)	Fe2—C16—C17—C18	59.79 (14)
Fe1—C6—C7—C8	−59.66 (13)	C20—C16—C17—Fe2	−59.61 (13)
C10—C6—C7—Fe1	59.81 (14)	C16—C17—C18—C19	−0.1 (2)
C6—C7—C8—C9	−0.2 (2)	Fe2—C17—C18—C19	59.00 (15)
Fe1—C7—C8—C9	−59.61 (14)	C16—C17—C18—Fe2	−59.13 (14)
C6—C7—C8—Fe1	59.38 (13)	C17—C18—C19—C20	0.0 (2)
C7—C8—C9—C10	0.2 (2)	Fe2—C18—C19—C20	58.75 (14)
Fe1—C8—C9—C10	−58.92 (14)	C17—C18—C19—Fe2	−58.72 (14)
C7—C8—C9—Fe1	59.13 (13)	C18—C19—C20—C16	0.1 (2)
C7—C6—C10—C9	0.0 (2)	Fe2—C19—C20—C16	59.23 (14)
Fe1—C6—C10—C9	59.62 (14)	C18—C19—C20—Fe2	−59.15 (15)
C7—C6—C10—Fe1	−59.64 (13)	C17—C16—C20—C19	−0.2 (2)
C8—C9—C10—C6	−0.1 (2)	Fe2—C16—C20—C19	−59.80 (14)
Fe1—C9—C10—C6	−59.14 (13)	C17—C16—C20—Fe2	59.63 (14)
C8—C9—C10—Fe1	59.02 (14)	C3—C2—C21—C22	−38.2 (2)
C5—C1—C11—C12	137.0 (2)	C1—C2—C21—C22	143.31 (18)
C2—C1—C11—C12	−55.7 (3)	Fe1—C2—C21—C22	51.2 (2)
Fe1—C1—C11—C12	44.1 (3)	C3—C2—C21—N1	88.0 (2)
C5—C1—C11—C15	−49.9 (3)	C1—C2—C21—N1	−90.4 (2)
C2—C1—C11—C15	117.3 (2)	Fe1—C2—C21—N1	177.44 (12)
Fe1—C1—C11—C15	−142.88 (17)	C23—N1—C21—C2	58.98 (19)
C5—C1—C11—Fe2	38.9 (3)	C24—N1—C21—C2	−60.3 (2)
C2—C1—C11—Fe2	−153.86 (15)	B1—N1—C21—C2	176.91 (15)
Fe1—C1—C11—Fe2	−54.1 (3)	C23—N1—C21—C22	−174.18 (16)
C15—C11—C12—C13	−0.6 (2)	C24—N1—C21—C22	66.6 (2)
C1—C11—C12—C13	173.31 (19)	B1—N1—C21—C22	−56.26 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···Br1	1.00	2.79	3.7154 (17)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯Br1	1.00	2.79	3.7154 (17)	154