1-Ferrocenyl-2-iodoethanone

The title compound, [Fe(C₅H₅)(C₇H₆IO)], crystallizes with two unique mol­ecules in the asymmetric unit. Both iodo substituents of the iodo­acetyl groups point away from the Fe atoms of the ferrocenyl groups. In the crystal structure, C—H...O hydrogen bonds and unusual I...π inter­actions stabilize the structure.

Key indicators

• Single-crystal X-ray study
• T = 85 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.018
• wR factor = 0.078
• Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  I1     ..  C14     ..       3.31 Ang.

Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  I2     ..  C24     ..       3.47 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H110   ..  O2      ..       2.67 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).

2-iodo-1-ferrocenylethanone

Crystal data

[Fe(C5H5)(C7H6IO)]	F(000) = 1360
Mr = 353.96	Dx = 2.017 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8585 reflections
a = 10.3689 (11) Å	θ = 2.8–27.6°
b = 10.6608 (12) Å	µ = 3.91 mm^−1
c = 21.370 (3) Å	T = 85 K
β = 99.252 (5)°	Rectangular plate, orange
V = 2331.5 (5) Å^3	0.38 × 0.18 × 0.08 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	5352 independent reflections
Radiation source: fine-focus sealed tube	5112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.470, Tmax = 0.731	k = −12→13
34186 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.31	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 1.3348P] where P = (Fo^2 + 2Fc^2)/3
5352 reflections	(Δ/σ)max = 0.004
271 parameters	Δρmax = 1.37 e Å^−3
0 restraints	Δρmin = −1.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C11	0.1272 (2)	0.1122 (3)	0.55302 (11)	0.0275 (5)
H11	0.1715	0.0970	0.5181	0.033*
C12	0.1090 (2)	0.2309 (2)	0.57997 (11)	0.0287 (5)
H12	0.1391	0.3091	0.5667	0.034*
C13	0.0372 (2)	0.2116 (2)	0.63075 (12)	0.0285 (5)
H13	0.0107	0.2752	0.6572	0.034*
C14	0.0122 (2)	0.0820 (3)	0.63508 (12)	0.0272 (5)
H14	−0.0339	0.0430	0.6648	0.033*
C15	0.0684 (2)	0.0200 (2)	0.58690 (11)	0.0265 (5)
H15	0.0667	−0.0677	0.5789	0.032*
Fe1	0.20842 (3)	0.11418 (3)	0.647769 (15)	0.01470 (8)
C16	0.40008 (19)	0.0666 (2)	0.65783 (9)	0.0147 (4)
C17	0.3322 (2)	−0.0177 (2)	0.69375 (9)	0.0180 (4)
H17	0.3252	−0.1060	0.6885	0.022*
C18	0.2774 (2)	0.0554 (2)	0.73867 (10)	0.0224 (4)
H18	0.2271	0.0242	0.7687	0.027*
C19	0.3111 (2)	0.1830 (2)	0.73086 (10)	0.0230 (4)
H19	0.2873	0.2513	0.7551	0.028*
C110	0.3862 (2)	0.1920 (2)	0.68084 (10)	0.0177 (4)
H110	0.4206	0.2665	0.6656	0.021*
C111	0.45486 (18)	0.02737 (18)	0.60170 (9)	0.0144 (4)
O1	0.46890 (16)	−0.08336 (14)	0.58972 (7)	0.0209 (3)
C112	0.49235 (19)	0.12820 (18)	0.55834 (10)	0.0143 (4)
H11A	0.4519	0.2092	0.5670	0.017*
H11B	0.4625	0.1054	0.5135	0.017*
I1	0.702620 (13)	0.142782 (13)	0.577182 (6)	0.01674 (7)
C21	0.7627 (2)	0.6439 (2)	0.56621 (10)	0.0221 (5)
H21	0.7021	0.6357	0.5281	0.027*
C22	0.7871 (2)	0.7547 (2)	0.60337 (11)	0.0240 (5)
H22	0.7446	0.8332	0.5947	0.029*
C23	0.8864 (2)	0.7271 (2)	0.65599 (11)	0.0251 (5)
H23	0.9225	0.7844	0.6881	0.030*
C24	0.9215 (2)	0.5993 (2)	0.65180 (12)	0.0247 (5)
H24	0.9849	0.5556	0.6809	0.030*
C25	0.8450 (2)	0.5475 (2)	0.59621 (10)	0.0229 (4)
H25	0.8486	0.4634	0.5819	0.027*
Fe2	0.72710 (3)	0.61423 (3)	0.657316 (14)	0.01354 (8)
C26	0.54039 (19)	0.55249 (19)	0.65350 (9)	0.0145 (4)
C27	0.5576 (2)	0.6719 (2)	0.68518 (9)	0.0171 (4)
H27	0.5115	0.7470	0.6725	0.021*
C28	0.6566 (2)	0.6565 (2)	0.73926 (10)	0.0212 (4)
H28	0.6875	0.7201	0.7690	0.025*
C29	0.7015 (2)	0.5304 (2)	0.74125 (10)	0.0214 (4)
H29	0.7675	0.4956	0.7724	0.026*
C210	0.6305 (2)	0.4654 (2)	0.68854 (10)	0.0177 (4)
H210	0.6408	0.3797	0.6783	0.021*
C211	0.46149 (18)	0.52427 (18)	0.59193 (9)	0.0136 (4)
O2	0.45486 (15)	0.41766 (14)	0.57006 (7)	0.0204 (3)
C212	0.3885 (2)	0.62926 (18)	0.55441 (10)	0.0150 (4)
H21A	0.3837	0.6137	0.5084	0.018*
H21B	0.4340	0.7100	0.5649	0.018*
I2	0.194293 (14)	0.636144 (15)	0.578744 (7)	0.02006 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0201 (11)	0.0435 (14)	0.0174 (10)	0.0009 (10)	−0.0018 (9)	−0.0003 (10)
C12	0.0229 (11)	0.0324 (13)	0.0288 (12)	0.0024 (10)	−0.0019 (9)	0.0110 (10)
C13	0.0177 (10)	0.0338 (13)	0.0331 (12)	0.0098 (9)	0.0017 (9)	0.0004 (10)
C14	0.0107 (9)	0.0378 (14)	0.0327 (13)	−0.0003 (9)	0.0018 (9)	0.0063 (10)
C15	0.0169 (10)	0.0314 (13)	0.0286 (12)	−0.0026 (9)	−0.0048 (9)	−0.0037 (10)
Fe1	0.01143 (15)	0.01907 (16)	0.01400 (15)	0.00065 (11)	0.00322 (11)	−0.00052 (11)
C16	0.0117 (9)	0.0184 (10)	0.0144 (9)	0.0001 (7)	0.0026 (7)	−0.0006 (8)
C17	0.0158 (9)	0.0220 (10)	0.0162 (9)	0.0013 (8)	0.0031 (7)	0.0028 (8)
C18	0.0192 (10)	0.0353 (13)	0.0133 (9)	0.0011 (9)	0.0043 (8)	0.0013 (9)
C19	0.0209 (10)	0.0309 (12)	0.0172 (10)	0.0018 (9)	0.0030 (8)	−0.0085 (9)
C110	0.0148 (9)	0.0195 (10)	0.0185 (9)	−0.0009 (8)	0.0017 (7)	−0.0047 (8)
C111	0.0118 (9)	0.0144 (9)	0.0171 (9)	−0.0006 (7)	0.0024 (7)	−0.0002 (7)
O1	0.0280 (8)	0.0133 (7)	0.0235 (8)	0.0012 (6)	0.0105 (6)	0.0001 (6)
C112	0.0120 (9)	0.0147 (9)	0.0164 (9)	0.0013 (7)	0.0029 (7)	0.0013 (7)
I1	0.01365 (9)	0.01857 (10)	0.01785 (10)	−0.00089 (4)	0.00206 (6)	0.00362 (5)
C21	0.0202 (11)	0.0312 (12)	0.0156 (10)	−0.0038 (8)	0.0046 (8)	0.0007 (8)
C22	0.0251 (11)	0.0227 (11)	0.0255 (11)	−0.0027 (9)	0.0081 (9)	0.0047 (9)
C23	0.0213 (11)	0.0301 (12)	0.0241 (11)	−0.0115 (9)	0.0043 (9)	−0.0026 (9)
C24	0.0138 (10)	0.0342 (13)	0.0262 (12)	−0.0006 (9)	0.0030 (9)	0.0005 (10)
C25	0.0183 (10)	0.0283 (12)	0.0232 (10)	0.0002 (9)	0.0069 (8)	−0.0025 (9)
Fe2	0.01176 (15)	0.01595 (15)	0.01244 (15)	−0.00119 (11)	0.00049 (11)	−0.00015 (11)
C26	0.0124 (9)	0.0163 (10)	0.0149 (9)	−0.0007 (7)	0.0023 (7)	0.0009 (7)
C27	0.0164 (9)	0.0198 (10)	0.0158 (9)	0.0009 (8)	0.0045 (7)	−0.0030 (8)
C28	0.0232 (11)	0.0268 (11)	0.0140 (9)	−0.0034 (9)	0.0046 (8)	−0.0038 (8)
C29	0.0198 (10)	0.0291 (12)	0.0141 (9)	−0.0021 (9)	−0.0009 (8)	0.0052 (8)
C210	0.0167 (9)	0.0180 (10)	0.0182 (9)	−0.0011 (8)	0.0018 (8)	0.0047 (8)
C211	0.0108 (8)	0.0140 (9)	0.0161 (9)	−0.0004 (7)	0.0028 (7)	0.0011 (7)
O2	0.0229 (8)	0.0136 (7)	0.0229 (8)	0.0008 (6)	−0.0022 (6)	−0.0016 (6)
C212	0.0132 (9)	0.0154 (9)	0.0168 (9)	0.0005 (7)	0.0034 (8)	0.0021 (7)
I2	0.01529 (10)	0.02496 (11)	0.02064 (10)	0.00449 (5)	0.00505 (7)	0.00229 (5)

Geometric parameters (Å, º)

C11—C12	1.415 (4)	C21—C25	1.421 (3)
C11—C15	1.415 (3)	C21—C22	1.423 (3)
C11—Fe1	2.064 (2)	C21—Fe2	2.064 (2)
C11—H11	0.9500	C21—H21	0.9500
C12—C13	1.426 (3)	C22—C23	1.428 (3)
C12—Fe1	2.056 (2)	C22—Fe2	2.046 (2)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.412 (4)	C23—C24	1.418 (4)
C13—Fe1	2.039 (2)	C23—Fe2	2.048 (2)
C13—H13	0.9500	C23—H23	0.9500
C14—C15	1.425 (3)	C24—C25	1.429 (3)
C14—Fe1	2.038 (2)	C24—Fe2	2.044 (2)
C14—H14	0.9500	C24—H24	0.9500
C15—Fe1	2.049 (2)	C25—Fe2	2.054 (2)
C15—H15	0.9500	C25—H25	0.9500
Fe1—C16	2.029 (2)	Fe2—C26	2.034 (2)
Fe1—C110	2.041 (2)	Fe2—C27	2.039 (2)
Fe1—C17	2.045 (2)	Fe2—C210	2.044 (2)
Fe1—C19	2.053 (2)	Fe2—C28	2.053 (2)
Fe1—C18	2.057 (2)	Fe2—C29	2.059 (2)
C16—C17	1.437 (3)	C26—C27	1.439 (3)
C16—C110	1.440 (3)	C26—C210	1.439 (3)
C16—C111	1.468 (3)	C26—C211	1.464 (3)
C17—C18	1.423 (3)	C27—C28	1.427 (3)
C17—H17	0.9500	C27—H27	0.9500
C18—C19	1.421 (3)	C28—C29	1.420 (3)
C18—H18	0.9500	C28—H28	0.9500
C19—C110	1.424 (3)	C29—C210	1.423 (3)
C19—H19	0.9500	C29—H29	0.9500
C110—H110	0.9500	C210—H210	0.9500
C111—O1	1.222 (2)	C211—O2	1.227 (2)
C111—C112	1.510 (3)	C211—C212	1.508 (3)
C112—I1	2.158 (2)	C212—I2	2.160 (2)
C112—H11A	0.9900	C212—H21A	0.9900
C112—H11B	0.9900	C212—H21B	0.9900
C12—C11—C15	108.4 (2)	C25—C21—C22	108.0 (2)
C12—C11—Fe1	69.62 (13)	C25—C21—Fe2	69.47 (12)
C15—C11—Fe1	69.31 (13)	C22—C21—Fe2	69.09 (12)
C12—C11—H11	125.8	C25—C21—H21	126.0
C15—C11—H11	125.8	C22—C21—H21	126.0
Fe1—C11—H11	126.8	Fe2—C21—H21	127.0
C11—C12—C13	107.5 (2)	C21—C22—C23	108.0 (2)
C11—C12—Fe1	70.21 (13)	C21—C22—Fe2	70.39 (13)
C13—C12—Fe1	68.95 (13)	C23—C22—Fe2	69.63 (13)
C11—C12—H12	126.2	C21—C22—H22	126.0
C13—C12—H12	126.2	C23—C22—H22	126.0
Fe1—C12—H12	126.2	Fe2—C22—H22	125.6
C14—C13—C12	108.3 (2)	C24—C23—C22	107.9 (2)
C14—C13—Fe1	69.73 (13)	C24—C23—Fe2	69.62 (13)
C12—C13—Fe1	70.29 (13)	C22—C23—Fe2	69.54 (13)
C14—C13—H13	125.8	C24—C23—H23	126.0
C12—C13—H13	125.8	C22—C23—H23	126.0
Fe1—C13—H13	125.7	Fe2—C23—H23	126.4
C13—C14—C15	107.8 (2)	C23—C24—C25	108.1 (2)
C13—C14—Fe1	69.75 (13)	C23—C24—Fe2	69.85 (13)
C15—C14—Fe1	70.02 (13)	C25—C24—Fe2	69.97 (12)
C13—C14—H14	126.1	C23—C24—H24	126.0
C15—C14—H14	126.1	C25—C24—H24	126.0
Fe1—C14—H14	125.7	Fe2—C24—H24	125.8
C11—C15—C14	108.0 (2)	C21—C25—C24	108.0 (2)
C11—C15—Fe1	70.44 (13)	C21—C25—Fe2	70.15 (13)
C14—C15—Fe1	69.19 (13)	C24—C25—Fe2	69.22 (13)
C11—C15—H15	126.0	C21—C25—H25	126.0
C14—C15—H15	126.0	C24—C25—H25	126.0
Fe1—C15—H15	125.9	Fe2—C25—H25	126.2
C16—Fe1—C14	155.77 (10)	C26—Fe2—C27	41.38 (8)
C16—Fe1—C13	163.06 (10)	C26—Fe2—C210	41.33 (8)
C14—Fe1—C13	40.52 (11)	C27—Fe2—C210	69.39 (9)
C16—Fe1—C110	41.44 (8)	C26—Fe2—C24	155.99 (10)
C14—Fe1—C110	160.24 (10)	C27—Fe2—C24	160.84 (9)
C13—Fe1—C110	124.52 (10)	C210—Fe2—C24	119.84 (9)
C16—Fe1—C17	41.30 (8)	C26—Fe2—C22	125.99 (9)
C14—Fe1—C17	118.96 (10)	C27—Fe2—C22	107.36 (9)
C13—Fe1—C17	153.79 (9)	C210—Fe2—C22	163.89 (9)
C110—Fe1—C17	69.57 (9)	C24—Fe2—C22	68.46 (10)
C16—Fe1—C15	121.77 (9)	C26—Fe2—C23	162.62 (9)
C14—Fe1—C15	40.79 (10)	C27—Fe2—C23	124.20 (9)
C13—Fe1—C15	68.19 (10)	C210—Fe2—C23	154.05 (9)
C110—Fe1—C15	157.96 (9)	C24—Fe2—C23	40.54 (10)
C17—Fe1—C15	107.11 (9)	C22—Fe2—C23	40.83 (9)
C16—Fe1—C19	68.59 (8)	C26—Fe2—C28	68.79 (8)
C14—Fe1—C19	122.88 (10)	C27—Fe2—C28	40.81 (8)
C13—Fe1—C19	106.73 (10)	C210—Fe2—C28	68.38 (9)
C110—Fe1—C19	40.68 (8)	C24—Fe2—C28	123.77 (10)
C17—Fe1—C19	68.40 (9)	C22—Fe2—C28	120.14 (9)
C15—Fe1—C19	160.00 (10)	C23—Fe2—C28	106.34 (9)
C16—Fe1—C12	126.70 (9)	C26—Fe2—C25	121.49 (9)
C14—Fe1—C12	68.37 (10)	C27—Fe2—C25	156.80 (9)
C13—Fe1—C12	40.76 (10)	C210—Fe2—C25	108.14 (9)
C110—Fe1—C12	108.70 (10)	C24—Fe2—C25	40.80 (9)
C17—Fe1—C12	163.54 (9)	C22—Fe2—C25	68.26 (9)
C15—Fe1—C12	67.99 (10)	C23—Fe2—C25	68.35 (10)
C19—Fe1—C12	121.65 (10)	C28—Fe2—C25	161.44 (9)
C16—Fe1—C18	68.75 (8)	C26—Fe2—C29	68.86 (8)
C14—Fe1—C18	105.22 (10)	C27—Fe2—C29	68.80 (9)
C13—Fe1—C18	118.98 (9)	C210—Fe2—C29	40.57 (8)
C110—Fe1—C18	68.86 (9)	C24—Fe2—C29	106.43 (9)
C17—Fe1—C18	40.60 (8)	C22—Fe2—C29	154.38 (9)
C15—Fe1—C18	123.61 (10)	C23—Fe2—C29	118.97 (9)
C19—Fe1—C18	40.45 (10)	C28—Fe2—C29	40.41 (9)
C12—Fe1—C18	155.30 (10)	C25—Fe2—C29	125.21 (9)
C16—Fe1—C11	109.84 (9)	C26—Fe2—C21	108.99 (9)
C14—Fe1—C11	68.09 (10)	C27—Fe2—C21	121.53 (9)
C13—Fe1—C11	67.92 (10)	C210—Fe2—C21	126.73 (9)
C110—Fe1—C11	123.15 (9)	C24—Fe2—C21	68.26 (10)
C17—Fe1—C11	126.14 (10)	C22—Fe2—C21	40.52 (9)
C15—Fe1—C11	40.25 (10)	C23—Fe2—C21	68.27 (9)
C19—Fe1—C11	157.65 (10)	C28—Fe2—C21	156.00 (9)
C12—Fe1—C11	40.18 (10)	C25—Fe2—C21	40.37 (9)
C18—Fe1—C11	161.49 (10)	C29—Fe2—C21	162.96 (9)
C17—C16—C110	108.27 (18)	C27—C26—C210	107.74 (18)
C17—C16—C111	123.09 (19)	C27—C26—C211	127.83 (18)
C110—C16—C111	128.04 (19)	C210—C26—C211	123.87 (18)
C17—C16—Fe1	69.96 (11)	C27—C26—Fe2	69.52 (11)
C110—C16—Fe1	69.75 (11)	C210—C26—Fe2	69.72 (11)
C111—C16—Fe1	119.06 (14)	C211—C26—Fe2	119.55 (13)
C18—C17—C16	107.56 (19)	C28—C27—C26	107.33 (18)
C18—C17—Fe1	70.16 (12)	C28—C27—Fe2	70.10 (12)
C16—C17—Fe1	68.74 (12)	C26—C27—Fe2	69.11 (11)
C18—C17—H17	126.2	C28—C27—H27	126.3
C16—C17—H17	126.2	C26—C27—H27	126.3
Fe1—C17—H17	126.4	Fe2—C27—H27	126.0
C19—C18—C17	108.18 (19)	C29—C28—C27	108.84 (19)
C19—C18—Fe1	69.63 (12)	C29—C28—Fe2	70.02 (12)
C17—C18—Fe1	69.25 (12)	C27—C28—Fe2	69.09 (12)
C19—C18—H18	125.9	C29—C28—H28	125.6
C17—C18—H18	125.9	C27—C28—H28	125.6
Fe1—C18—H18	126.8	Fe2—C28—H28	126.9
C18—C19—C110	109.12 (19)	C28—C29—C210	108.17 (19)
C18—C19—Fe1	69.92 (12)	C28—C29—Fe2	69.56 (12)
C110—C19—Fe1	69.21 (12)	C210—C29—Fe2	69.16 (12)
C18—C19—H19	125.4	C28—C29—H29	125.9
C110—C19—H19	125.4	C210—C29—H29	125.9
Fe1—C19—H19	127.0	Fe2—C29—H29	126.9
C19—C110—C16	106.87 (19)	C29—C210—C26	107.93 (19)
C19—C110—Fe1	70.11 (12)	C29—C210—Fe2	70.26 (12)
C16—C110—Fe1	68.81 (11)	C26—C210—Fe2	68.95 (11)
C19—C110—H110	126.6	C29—C210—H210	126.0
C16—C110—H110	126.6	C26—C210—H210	126.0
Fe1—C110—H110	126.1	Fe2—C210—H210	126.3
O1—C111—C16	121.41 (18)	O2—C211—C26	121.44 (18)
O1—C111—C112	120.53 (18)	O2—C211—C212	119.52 (18)
C16—C111—C112	118.05 (17)	C26—C211—C212	119.04 (17)
C111—C112—I1	106.79 (13)	C211—C212—I2	107.75 (13)
C111—C112—H11A	110.4	C211—C212—H21A	110.2
I1—C112—H11A	110.4	I2—C212—H21A	110.2
C111—C112—H11B	110.4	C211—C212—H21B	110.2
I1—C112—H11B	110.4	I2—C212—H21B	110.2
H11A—C112—H11B	108.6	H21A—C212—H21B	108.5
C15—C11—C12—C13	−0.4 (3)	C25—C21—C22—C23	1.0 (2)
Fe1—C11—C12—C13	−59.06 (16)	Fe2—C21—C22—C23	59.70 (15)
C15—C11—C12—Fe1	58.62 (16)	C25—C21—C22—Fe2	−58.75 (15)
C11—C12—C13—C14	0.3 (3)	C21—C22—C23—C24	−0.9 (3)
Fe1—C12—C13—C14	−59.58 (16)	Fe2—C22—C23—C24	59.23 (16)
C11—C12—C13—Fe1	59.85 (16)	C21—C22—C23—Fe2	−60.18 (15)
C12—C13—C14—C15	0.0 (3)	C22—C23—C24—C25	0.6 (3)
Fe1—C13—C14—C15	−59.94 (15)	Fe2—C23—C24—C25	59.76 (15)
C12—C13—C14—Fe1	59.93 (16)	C22—C23—C24—Fe2	−59.18 (15)
C12—C11—C15—C14	0.4 (3)	C22—C21—C25—C24	−0.6 (2)
Fe1—C11—C15—C14	59.24 (16)	Fe2—C21—C25—C24	−59.11 (15)
C12—C11—C15—Fe1	−58.81 (16)	C22—C21—C25—Fe2	58.52 (15)
C13—C14—C15—C11	−0.3 (3)	C23—C24—C25—C21	0.0 (3)
Fe1—C14—C15—C11	−60.03 (16)	Fe2—C24—C25—C21	59.69 (15)
C13—C14—C15—Fe1	59.77 (16)	C23—C24—C25—Fe2	−59.69 (16)
C13—C14—Fe1—C16	−171.1 (2)	C23—C24—Fe2—C26	169.58 (19)
C15—C14—Fe1—C16	−52.3 (3)	C25—C24—Fe2—C26	50.5 (3)
C15—C14—Fe1—C13	118.7 (2)	C23—C24—Fe2—C27	−43.1 (3)
C13—C14—Fe1—C110	47.4 (3)	C25—C24—Fe2—C27	−162.1 (2)
C15—C14—Fe1—C110	166.1 (3)	C23—C24—Fe2—C210	−157.55 (13)
C13—C14—Fe1—C17	158.54 (14)	C25—C24—Fe2—C210	83.39 (16)
C15—C14—Fe1—C17	−82.73 (16)	C23—C24—Fe2—C22	37.80 (14)
C13—C14—Fe1—C15	−118.7 (2)	C25—C24—Fe2—C22	−81.25 (15)
C13—C14—Fe1—C19	76.78 (17)	C25—C24—Fe2—C23	−119.1 (2)
C15—C14—Fe1—C19	−164.50 (14)	C23—C24—Fe2—C28	−74.87 (16)
C13—C14—Fe1—C12	−37.79 (15)	C25—C24—Fe2—C28	166.07 (14)
C15—C14—Fe1—C12	80.93 (16)	C23—C24—Fe2—C25	119.1 (2)
C13—C14—Fe1—C18	117.03 (15)	C23—C24—Fe2—C29	−115.60 (14)
C15—C14—Fe1—C18	−124.25 (15)	C25—C24—Fe2—C29	125.34 (14)
C13—C14—Fe1—C11	−81.20 (16)	C23—C24—Fe2—C21	81.55 (15)
C15—C14—Fe1—C11	37.52 (15)	C25—C24—Fe2—C21	−37.51 (14)
C14—C13—Fe1—C16	167.4 (3)	C21—C22—Fe2—C26	−76.66 (16)
C12—C13—Fe1—C16	48.1 (4)	C23—C22—Fe2—C26	164.49 (13)
C12—C13—Fe1—C14	−119.2 (2)	C21—C22—Fe2—C27	−118.53 (14)
C14—C13—Fe1—C110	−162.42 (14)	C23—C22—Fe2—C27	122.61 (14)
C12—C13—Fe1—C110	78.34 (17)	C21—C22—Fe2—C210	−42.8 (4)
C14—C13—Fe1—C17	−46.4 (3)	C23—C22—Fe2—C210	−161.7 (3)
C12—C13—Fe1—C17	−165.68 (19)	C21—C22—Fe2—C24	81.32 (15)
C14—C13—Fe1—C15	38.10 (15)	C23—C22—Fe2—C24	−37.54 (14)
C12—C13—Fe1—C15	−81.14 (16)	C21—C22—Fe2—C23	118.9 (2)
C14—C13—Fe1—C19	−121.39 (15)	C21—C22—Fe2—C28	−161.18 (14)
C12—C13—Fe1—C19	119.37 (15)	C23—C22—Fe2—C28	79.96 (16)
C14—C13—Fe1—C12	119.2 (2)	C21—C22—Fe2—C25	37.26 (13)
C14—C13—Fe1—C18	−79.28 (17)	C23—C22—Fe2—C25	−81.59 (15)
C12—C13—Fe1—C18	161.48 (15)	C21—C22—Fe2—C29	164.43 (19)
C14—C13—Fe1—C11	81.65 (16)	C23—C22—Fe2—C29	45.6 (3)
C12—C13—Fe1—C11	−37.60 (15)	C23—C22—Fe2—C21	−118.9 (2)
C11—C15—Fe1—C16	−83.47 (16)	C24—C23—Fe2—C26	−165.7 (3)
C14—C15—Fe1—C16	157.53 (14)	C22—C23—Fe2—C26	−46.4 (3)
C11—C15—Fe1—C14	119.0 (2)	C24—C23—Fe2—C27	164.28 (13)
C11—C15—Fe1—C13	81.15 (16)	C22—C23—Fe2—C27	−76.42 (16)
C14—C15—Fe1—C13	−37.86 (15)	C24—C23—Fe2—C210	49.2 (3)
C11—C15—Fe1—C110	−48.5 (3)	C22—C23—Fe2—C210	168.50 (19)
C14—C15—Fe1—C110	−167.5 (2)	C22—C23—Fe2—C24	119.3 (2)
C11—C15—Fe1—C17	−126.25 (14)	C24—C23—Fe2—C22	−119.3 (2)
C14—C15—Fe1—C17	114.75 (15)	C24—C23—Fe2—C28	123.25 (14)
C11—C15—Fe1—C19	160.0 (3)	C22—C23—Fe2—C28	−117.45 (14)
C14—C15—Fe1—C19	41.0 (3)	C24—C23—Fe2—C25	−37.92 (14)
C11—C15—Fe1—C12	37.06 (14)	C22—C23—Fe2—C25	81.38 (15)
C14—C15—Fe1—C12	−81.95 (16)	C24—C23—Fe2—C29	81.37 (16)
C11—C15—Fe1—C18	−167.72 (14)	C22—C23—Fe2—C29	−159.33 (14)
C14—C15—Fe1—C18	73.28 (17)	C24—C23—Fe2—C21	−81.52 (15)
C14—C15—Fe1—C11	−119.0 (2)	C22—C23—Fe2—C21	37.77 (14)
C11—C12—Fe1—C16	76.90 (17)	C21—C25—Fe2—C26	82.45 (15)
C13—C12—Fe1—C16	−164.30 (14)	C24—C25—Fe2—C26	−158.38 (14)
C11—C12—Fe1—C14	−81.22 (16)	C21—C25—Fe2—C27	46.0 (3)
C13—C12—Fe1—C14	37.58 (15)	C24—C25—Fe2—C27	165.2 (2)
C11—C12—Fe1—C13	−118.8 (2)	C21—C25—Fe2—C210	125.89 (13)
C11—C12—Fe1—C110	119.61 (14)	C24—C25—Fe2—C210	−114.94 (15)
C13—C12—Fe1—C110	−121.59 (15)	C21—C25—Fe2—C24	−119.2 (2)
C11—C12—Fe1—C17	38.5 (4)	C21—C25—Fe2—C22	−37.39 (13)
C13—C12—Fe1—C17	157.3 (3)	C24—C25—Fe2—C22	81.78 (15)
C11—C12—Fe1—C15	−37.12 (14)	C21—C25—Fe2—C23	−81.49 (15)
C13—C12—Fe1—C15	81.68 (16)	C24—C25—Fe2—C23	37.68 (14)
C11—C12—Fe1—C19	162.57 (14)	C21—C25—Fe2—C28	−158.1 (3)
C13—C12—Fe1—C19	−78.63 (17)	C24—C25—Fe2—C28	−38.9 (4)
C11—C12—Fe1—C18	−160.5 (2)	C21—C25—Fe2—C29	167.56 (13)
C13—C12—Fe1—C18	−41.7 (3)	C24—C25—Fe2—C29	−73.28 (17)
C13—C12—Fe1—C11	118.8 (2)	C24—C25—Fe2—C21	119.2 (2)
C12—C11—Fe1—C16	−123.88 (14)	C25—C21—Fe2—C26	−116.63 (14)
C15—C11—Fe1—C16	116.12 (14)	C22—C21—Fe2—C26	123.63 (14)
C12—C11—Fe1—C14	81.99 (16)	C25—C21—Fe2—C27	−160.58 (13)
C15—C11—Fe1—C14	−38.01 (15)	C22—C21—Fe2—C27	79.68 (16)
C12—C11—Fe1—C13	38.13 (15)	C25—C21—Fe2—C210	−73.86 (16)
C15—C11—Fe1—C13	−81.88 (16)	C22—C21—Fe2—C210	166.39 (13)
C12—C11—Fe1—C110	−79.62 (16)	C25—C21—Fe2—C24	37.90 (14)
C15—C11—Fe1—C110	160.38 (14)	C22—C21—Fe2—C24	−81.84 (15)
C12—C11—Fe1—C17	−167.37 (13)	C25—C21—Fe2—C22	119.74 (19)
C15—C11—Fe1—C17	72.62 (17)	C25—C21—Fe2—C23	81.69 (15)
C12—C11—Fe1—C15	120.0 (2)	C22—C21—Fe2—C23	−38.05 (14)
C12—C11—Fe1—C19	−42.1 (3)	C25—C21—Fe2—C28	163.0 (2)
C15—C11—Fe1—C19	−162.1 (2)	C22—C21—Fe2—C28	43.3 (3)
C15—C11—Fe1—C12	−120.0 (2)	C22—C21—Fe2—C25	−119.74 (19)
C12—C11—Fe1—C18	153.9 (3)	C25—C21—Fe2—C29	−36.9 (4)
C15—C11—Fe1—C18	33.9 (4)	C22—C21—Fe2—C29	−156.7 (3)
C14—Fe1—C16—C17	−42.1 (3)	C210—Fe2—C26—C27	119.00 (17)
C13—Fe1—C16—C17	158.1 (3)	C24—Fe2—C26—C27	164.5 (2)
C110—Fe1—C16—C17	119.35 (17)	C22—Fe2—C26—C27	−74.54 (15)
C15—Fe1—C16—C17	−79.59 (15)	C23—Fe2—C26—C27	−38.7 (3)
C19—Fe1—C16—C17	81.22 (13)	C28—Fe2—C26—C27	38.03 (12)
C12—Fe1—C16—C17	−164.54 (13)	C25—Fe2—C26—C27	−159.27 (12)
C18—Fe1—C16—C17	37.65 (12)	C29—Fe2—C26—C27	81.52 (13)
C11—Fe1—C16—C17	−122.63 (13)	C21—Fe2—C26—C27	−116.49 (13)
C14—Fe1—C16—C110	−161.5 (2)	C27—Fe2—C26—C210	−119.00 (17)
C13—Fe1—C16—C110	38.8 (4)	C24—Fe2—C26—C210	45.5 (3)
C17—Fe1—C16—C110	−119.35 (17)	C22—Fe2—C26—C210	166.47 (13)
C15—Fe1—C16—C110	161.05 (13)	C23—Fe2—C26—C210	−157.7 (3)
C19—Fe1—C16—C110	−38.14 (13)	C28—Fe2—C26—C210	−80.96 (13)
C12—Fe1—C16—C110	76.11 (16)	C25—Fe2—C26—C210	81.74 (14)
C18—Fe1—C16—C110	−81.71 (13)	C29—Fe2—C26—C210	−37.48 (12)
C11—Fe1—C16—C110	118.02 (14)	C21—Fe2—C26—C210	124.51 (13)
C14—Fe1—C16—C111	75.4 (3)	C27—Fe2—C26—C211	122.7 (2)
C13—Fe1—C16—C111	−84.3 (4)	C210—Fe2—C26—C211	−118.3 (2)
C110—Fe1—C16—C111	−123.1 (2)	C24—Fe2—C26—C211	−72.8 (3)
C17—Fe1—C16—C111	117.5 (2)	C22—Fe2—C26—C211	48.2 (2)
C15—Fe1—C16—C111	37.9 (2)	C23—Fe2—C26—C211	84.0 (3)
C19—Fe1—C16—C111	−161.26 (19)	C28—Fe2—C26—C211	160.78 (19)
C12—Fe1—C16—C111	−47.0 (2)	C25—Fe2—C26—C211	−36.5 (2)
C18—Fe1—C16—C111	155.17 (19)	C29—Fe2—C26—C211	−155.74 (18)
C11—Fe1—C16—C111	−5.11 (19)	C21—Fe2—C26—C211	6.25 (18)
C110—C16—C17—C18	−0.2 (2)	C210—C26—C27—C28	−0.5 (2)
C111—C16—C17—C18	−171.96 (19)	C211—C26—C27—C28	−172.07 (19)
Fe1—C16—C17—C18	−59.66 (14)	Fe2—C26—C27—C28	−59.95 (14)
C110—C16—C17—Fe1	59.44 (14)	C210—C26—C27—Fe2	59.47 (14)
C111—C16—C17—Fe1	−112.30 (19)	C211—C26—C27—Fe2	−112.1 (2)
C16—Fe1—C17—C18	118.98 (18)	C26—Fe2—C27—C28	118.50 (18)
C14—Fe1—C17—C18	−79.36 (16)	C210—Fe2—C27—C28	80.40 (14)
C13—Fe1—C17—C18	−46.8 (3)	C24—Fe2—C27—C28	−42.1 (3)
C110—Fe1—C17—C18	80.98 (14)	C22—Fe2—C27—C28	−116.29 (14)
C15—Fe1—C17—C18	−122.05 (14)	C23—Fe2—C27—C28	−74.55 (16)
C19—Fe1—C17—C18	37.27 (13)	C25—Fe2—C27—C28	168.5 (2)
C12—Fe1—C17—C18	167.9 (3)	C29—Fe2—C27—C28	36.83 (13)
C11—Fe1—C17—C18	−162.23 (14)	C21—Fe2—C27—C28	−158.34 (13)
C14—Fe1—C17—C16	161.66 (13)	C210—Fe2—C27—C26	−38.10 (12)
C13—Fe1—C17—C16	−165.8 (2)	C24—Fe2—C27—C26	−160.6 (3)
C110—Fe1—C17—C16	−38.00 (12)	C22—Fe2—C27—C26	125.21 (12)
C15—Fe1—C17—C16	118.97 (13)	C23—Fe2—C27—C26	166.95 (12)
C19—Fe1—C17—C16	−81.70 (13)	C28—Fe2—C27—C26	−118.50 (18)
C12—Fe1—C17—C16	48.9 (4)	C25—Fe2—C27—C26	50.0 (3)
C18—Fe1—C17—C16	−118.98 (18)	C29—Fe2—C27—C26	−81.67 (13)
C11—Fe1—C17—C16	78.79 (15)	C21—Fe2—C27—C26	83.16 (14)
C16—C17—C18—C19	−0.1 (2)	C26—C27—C28—C29	0.4 (2)
Fe1—C17—C18—C19	−58.92 (15)	Fe2—C27—C28—C29	−58.88 (15)
C16—C17—C18—Fe1	58.77 (14)	C26—C27—C28—Fe2	59.32 (14)
C16—Fe1—C18—C19	81.50 (13)	C26—Fe2—C28—C29	81.90 (14)
C14—Fe1—C18—C19	−123.24 (14)	C27—Fe2—C28—C29	120.44 (19)
C13—Fe1—C18—C19	−81.82 (15)	C210—Fe2—C28—C29	37.35 (12)
C110—Fe1—C18—C19	36.90 (13)	C24—Fe2—C28—C29	−74.91 (16)
C17—Fe1—C18—C19	119.78 (18)	C22—Fe2—C28—C29	−157.87 (13)
C15—Fe1—C18—C19	−163.66 (13)	C23—Fe2—C28—C29	−115.73 (14)
C12—Fe1—C18—C19	−52.1 (3)	C25—Fe2—C28—C29	−45.3 (3)
C11—Fe1—C18—C19	170.7 (3)	C21—Fe2—C28—C29	171.1 (2)
C16—Fe1—C18—C17	−38.28 (12)	C26—Fe2—C28—C27	−38.54 (12)
C14—Fe1—C18—C17	116.98 (14)	C210—Fe2—C28—C27	−83.09 (13)
C13—Fe1—C18—C17	158.40 (13)	C24—Fe2—C28—C27	164.65 (13)
C110—Fe1—C18—C17	−82.88 (13)	C22—Fe2—C28—C27	81.69 (15)
C15—Fe1—C18—C17	76.56 (15)	C23—Fe2—C28—C27	123.82 (14)
C19—Fe1—C18—C17	−119.78 (18)	C25—Fe2—C28—C27	−165.7 (3)
C12—Fe1—C18—C17	−171.8 (2)	C29—Fe2—C28—C27	−120.44 (19)
C11—Fe1—C18—C17	50.9 (3)	C21—Fe2—C28—C27	50.7 (3)
C17—C18—C19—C110	0.5 (2)	C27—C28—C29—C210	−0.2 (2)
Fe1—C18—C19—C110	−58.21 (15)	Fe2—C28—C29—C210	−58.54 (15)
C17—C18—C19—Fe1	58.68 (15)	C27—C28—C29—Fe2	58.31 (15)
C16—Fe1—C19—C18	−81.95 (14)	C26—Fe2—C29—C28	−81.71 (14)
C14—Fe1—C19—C18	73.95 (16)	C27—Fe2—C29—C28	−37.18 (13)
C13—Fe1—C19—C18	115.28 (14)	C210—Fe2—C29—C28	−119.86 (18)
C110—Fe1—C19—C18	−120.79 (19)	C24—Fe2—C29—C28	123.20 (14)
C17—Fe1—C19—C18	−37.41 (12)	C22—Fe2—C29—C28	48.9 (3)
C15—Fe1—C19—C18	43.2 (3)	C23—Fe2—C29—C28	81.14 (15)
C12—Fe1—C19—C18	157.22 (13)	C25—Fe2—C29—C28	163.92 (13)
C11—Fe1—C19—C18	−172.2 (2)	C21—Fe2—C29—C28	−167.6 (3)
C16—Fe1—C19—C110	38.83 (13)	C26—Fe2—C29—C210	38.15 (12)
C14—Fe1—C19—C110	−165.27 (14)	C27—Fe2—C29—C210	82.68 (13)
C13—Fe1—C19—C110	−123.93 (14)	C24—Fe2—C29—C210	−116.94 (14)
C17—Fe1—C19—C110	83.38 (14)	C22—Fe2—C29—C210	168.74 (19)
C15—Fe1—C19—C110	164.0 (3)	C23—Fe2—C29—C210	−159.00 (13)
C12—Fe1—C19—C110	−81.99 (16)	C28—Fe2—C29—C210	119.86 (18)
C18—Fe1—C19—C110	120.79 (19)	C25—Fe2—C29—C210	−76.21 (15)
C11—Fe1—C19—C110	−51.4 (3)	C21—Fe2—C29—C210	−47.8 (4)
C18—C19—C110—C16	−0.6 (2)	C28—C29—C210—C26	−0.1 (2)
Fe1—C19—C110—C16	−59.24 (14)	Fe2—C29—C210—C26	−58.86 (14)
C18—C19—C110—Fe1	58.65 (15)	C28—C29—C210—Fe2	58.79 (15)
C17—C16—C110—C19	0.5 (2)	C27—C26—C210—C29	0.3 (2)
C111—C16—C110—C19	171.7 (2)	C211—C26—C210—C29	172.34 (18)
Fe1—C16—C110—C19	60.07 (14)	Fe2—C26—C210—C29	59.68 (14)
C17—C16—C110—Fe1	−59.57 (14)	C27—C26—C210—Fe2	−59.34 (14)
C111—C16—C110—Fe1	111.6 (2)	C211—C26—C210—Fe2	112.66 (19)
C16—Fe1—C110—C19	−118.12 (18)	C26—Fe2—C210—C29	−119.24 (18)
C14—Fe1—C110—C19	39.2 (3)	C27—Fe2—C210—C29	−81.09 (13)
C13—Fe1—C110—C19	74.68 (17)	C24—Fe2—C210—C29	80.30 (15)
C17—Fe1—C110—C19	−80.25 (14)	C22—Fe2—C210—C29	−162.3 (3)
C15—Fe1—C110—C19	−165.5 (2)	C23—Fe2—C210—C29	45.8 (3)
C12—Fe1—C110—C19	117.13 (15)	C28—Fe2—C210—C29	−37.21 (13)
C18—Fe1—C110—C19	−36.70 (14)	C25—Fe2—C210—C29	123.39 (13)
C11—Fe1—C110—C19	159.20 (14)	C21—Fe2—C210—C29	164.29 (13)
C14—Fe1—C110—C16	157.3 (3)	C27—Fe2—C210—C26	38.14 (12)
C13—Fe1—C110—C16	−167.20 (13)	C24—Fe2—C210—C26	−160.46 (12)
C17—Fe1—C110—C16	37.87 (12)	C22—Fe2—C210—C26	−43.0 (4)
C15—Fe1—C110—C16	−47.4 (3)	C23—Fe2—C210—C26	164.99 (19)
C19—Fe1—C110—C16	118.12 (18)	C28—Fe2—C210—C26	82.03 (13)
C12—Fe1—C110—C16	−124.75 (13)	C25—Fe2—C210—C26	−117.38 (13)
C18—Fe1—C110—C16	81.42 (13)	C29—Fe2—C210—C26	119.24 (18)
C11—Fe1—C110—C16	−82.68 (15)	C21—Fe2—C210—C26	−76.47 (15)
C17—C16—C111—O1	−14.9 (3)	C27—C26—C211—O2	−179.9 (2)
C110—C16—C111—O1	175.1 (2)	C210—C26—C211—O2	9.8 (3)
Fe1—C16—C111—O1	−98.8 (2)	Fe2—C26—C211—O2	94.1 (2)
C17—C16—C111—C112	164.43 (18)	C27—C26—C211—C212	0.9 (3)
C110—C16—C111—C112	−5.6 (3)	C210—C26—C211—C212	−169.39 (18)
Fe1—C16—C111—C112	80.5 (2)	Fe2—C26—C211—C212	−85.1 (2)
O1—C111—C112—I1	−76.8 (2)	O2—C211—C212—I2	88.32 (19)
C16—C111—C112—I1	103.92 (17)	C26—C211—C212—I2	−92.51 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C110—H110···O2	0.95	2.67	3.527 (3)	151
C112—H11A···O2	0.99	2.22	3.125 (2)	151
C212—H21B···O1^i	0.99	2.28	3.232 (3)	161
C27—H27···O1^i	0.95	2.52	3.349 (3)	146

Symmetry code: (i) x, y+1, z.