metal-organic papers
Acta Cryst.(2004). E60, m1961±m1962 doi:10.1107/S1600536804030491 Jian, Ma, Sun and Xiao [Fe(C5H5)(C12H9O2)]
m1961
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Ferrocenylbenzoic acid
Fangfang Jian,* Huaibo Ma, Pingping Sun and Hailian Xiao
New Materials and Function, Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao, 266042, People's Republic of China
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.010 AÊ
Rfactor = 0.055
wRfactor = 0.150
Data-to-parameter ratio = 13.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
In the title compound, [Fe(C5H5)(C12H9O2)], there exists an
extended conjugated system between the benzoic and cyclo-pentadienyl rings. The packing is stabilized by OH O hydrogen bonds.
Comment
The study of ferrocene compounds opened up a new ®eld of organometallic chemistry and has increased during the last two decades (Guo et al., 2004). As non-benzenoid aromatic complexes, the physical and chemical properties of ferrocene compounds show unaccustomed variety due to the existence of the iron atom. They are used as combustion-improving agents for the solid propellant of hydroxyl-terminated polybutadiene binders, which contribute greatly to their fast development. In order to further explore this kind of complex, we report here the crystal structure of the title compound, (I).
In the title compound, the CÐC bond lengths of the cyclopentadienyl rings are in good agreement with the values reported for other ferrocene derivatives (Wang et al., 1970; Guoet al., 2004). The Fe±C distances are also in good agree-ment with reported values (Dunitzet al., 1956). The distances of the Fe atom from the centroids of the substituted and unsubstituted cyclopentadienyl rings [1.647 (2) and 1.642 (2) AÊ, respectively] are a little shorter than those found in ferrocene [1.660 (2) AÊ]. The C8ÐC11 bond distance [1.465 (8) AÊ] suggests partial double-bond character, indi-cating conjugation between the benzene and cyclopentadienyl rings. The dihedral angle between the C1±C5 and C6±C10 cyclopentadienyl rings of the ferrocene and the benzene ring are 5.61 (2) and 6.32 (2), respectively. There is an
inter-molecular OH O hydrogen bond, which stabilizes the crystal structure (Table 1).
Experimental
The title compound was synthesized by reaction ofp-aminobenzoic acid (0.07 mol), sodium nitrite (0.072 mol), HCl (140 ml, 4.3M) and ferrocene (0.072 mol) at 273±278 K for 1 h. Single crystals suitable for
X-ray measurements were obtained by recrystallization from methanol at room temperature.
Crystal data
[Fe(C5H5)(C12H9O2)]
Mr= 306.13 Monoclinic,P21=c
a= 7.8880 (16) AÊ
b= 16.006 (3) AÊ
c= 11.579 (4) AÊ
= 115.38 (2) V= 1320.8 (6) AÊ3
Z= 4
Dx= 1.539 Mg mÿ3
MoKradiation Cell parameters from 25
re¯ections
= 4±14
= 1.14 mmÿ1
T= 293 (2) K Pillar, red
0.200.200.18 mm
Data collection
Enraf±Nonius CAD-4 diffractometer
!scans
Absorption correction: none 2768 measured re¯ections 2578 independent re¯ections 1192 re¯ections withI> 2(I)
Rint= 0.095
max= 26.0
h=ÿ9!0
k=ÿ19!0
l=ÿ12!14 3 standard re¯ections
every 100 re¯ections intensity decay: none
Refinement
Re®nement onF2
R[F2> 2(F2)] = 0.055
wR(F2) = 0.150
S= 0.96 2578 re¯ections 197 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(Fo2) + (0.0611P)2
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.49 e AÊÿ3 min=ÿ0.43 e AÊÿ3
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O1ÐH1B O2i 0.81 (6) 1.86 (6) 2.646 (6) 162 (7)
Symmetry code: (i)ÿ2ÿx;1ÿy;ÿ2ÿz.
Carbon-bound H atoms were positioned geometrically and re®ned as riding, with CÐH = 0.93±0.98 AÊ andUiso(H) = 1.2 timesUeq(C).
The H atom attached to oxygen was located in a difference map and freely re®ned.
Data collection: CAD-4 Software (Enraf±Nonius, 1989); cell re®nement:CAD-4Software; data reduction:NRCVAX(Gabeet al., 1989; program(s) used to solve structure:SHELXTL/PC(Sheldrick, 1990); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:SHELXTL/PC; software used to prepare material for publication:WinGX(Farrugia, 1999).
The authors thank the Natural Science Foundation of Shandong Province (No.Y2002B06) and the Science Research Foundation of Qingdao University of Science and Technology (No. 03Z08).
References
Dunitz, J. D., Orgel, L. E. & Rich, A. (1956).Acta Cryst.9, 373±375. Enraf±Nonius (1989).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The
Netherlands.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837±838.
Gabe, E. J., Le Page, Y., Charland, J. P., Lee, F. L., White, P. S. (1989).J. Appl. Cryst.22, 384±387.
Guo, H. X., Huang, Z. X., Chen, J. X. (2004).Chin. J. Struct. Chem.23, 153± 156.
Sheldrick, G. M. (1990).SHELXTL-PC. Siemens Analytical X-ray Instru-ments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Wang, M. F., Bu, X. R., Meng, Q. J., You, X. Z. (1970).Chin. J. Appl. Chem.7,
82±84.
Figure 1
supporting information
sup-1
Acta Cryst. (2004). E60, m1961–m1962
supporting information
Acta Cryst. (2004). E60, m1961–m1962 [https://doi.org/10.1107/S1600536804030491]
Ferrocenylbenzoic acid
Fangfang Jian, Huaibo Ma, Pingping Sun and Hailian Xiao
(I)
Crystal data
[Fe(C5H4)2(C12H9O2)] Mr = 306.13
Monoclinic, P21/c
Hall symbol: -P 2y bc a = 7.8880 (16) Å b = 16.006 (3) Å c = 11.579 (4) Å β = 115.38 (2)° V = 1320.8 (6) Å3 Z = 4
F(000) = 632 Dx = 1.539 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 4–14°
µ = 1.14 mm−1 T = 293 K Pillar, red
0.20 × 0.20 × 0.18 mm
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
2768 measured reflections 2578 independent reflections 1192 reflections with I > 2σ(I)
Rint = 0.095
θmax = 26.0°, θmin = 2.3° h = −9→0
k = −19→0 l = −12→14
3 standard reflections every 100 reflections intensity decay: none
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.055 wR(F2) = 0.150 S = 0.96 2578 reflections 197 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0611P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.49 e Å−3
Δρmin = −0.43 e Å−3
Special details
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 (Å2)
x y z Uiso*/Ueq
Fe1 −0.59197 (12) 0.30644 (5) −0.18828 (8) 0.0404 (3)
O1 −1.0802 (7) 0.4280 (3) −0.9117 (4) 0.0665 (15)
H1B −1.089 (10) 0.435 (5) −0.981 (7) 0.080*
O2 −0.8561 (6) 0.5250 (3) −0.8536 (4) 0.0644 (13)
C1 −0.3482 (10) 0.2496 (4) −0.0750 (7) 0.061 (2)
H1A −0.2668 0.2645 0.0138 0.10 (3)*
C2 −0.3363 (9) 0.2827 (4) −0.1850 (7) 0.0596 (19)
H2A −0.2457 0.3243 −0.1860 0.043 (16)*
C3 −0.4779 (10) 0.2446 (4) −0.2913 (6) 0.0573 (18)
H3A −0.5051 0.2560 −0.3807 0.041 (15)*
C4 −0.5747 (11) 0.1879 (4) −0.2501 (6) 0.0624 (19)
H4A −0.6803 0.1527 −0.3047 0.040 (16)*
C5 −0.4946 (10) 0.1918 (4) −0.1146 (6) 0.0597 (18)
H5A −0.5338 0.1592 −0.0586 0.08 (2)*
C6 −0.7816 (10) 0.3411 (4) −0.1210 (6) 0.0580 (18)
H6A −0.8206 0.3082 −0.0653 0.025 (12)*
C7 −0.8663 (9) 0.3406 (5) −0.2562 (6) 0.0577 (18)
H7A −0.9736 0.3061 −0.3104 0.08 (2)*
C8 −0.7679 (8) 0.3971 (4) −0.3011 (6) 0.0460 (15)
C9 −0.6212 (9) 0.4324 (4) −0.1910 (6) 0.0491 (16)
H9A −0.5288 0.4732 −0.1913 0.039 (16)*
C10 −0.6311 (10) 0.3993 (4) −0.0813 (6) 0.0578 (19)
H10A −0.5462 0.4129 0.0074 0.06 (2)*
C11 −0.8125 (8) 0.4154 (4) −0.4351 (6) 0.0444 (15)
C12 −0.9478 (8) 0.3691 (4) −0.5344 (6) 0.0495 (16)
H12A −1.0082 0.3251 −0.5150 0.062 (19)*
C13 −0.9931 (9) 0.3878 (4) −0.6606 (6) 0.0509 (17)
H13A −1.0859 0.3571 −0.7250 0.053 (18)*
C14 −0.9014 (9) 0.4519 (4) −0.6927 (6) 0.0436 (15)
C15 −0.7704 (8) 0.4980 (4) −0.5948 (6) 0.0480 (16)
H15A −0.7102 0.5421 −0.6140 0.050 (18)*
C16 −0.7268 (8) 0.4802 (4) −0.4695 (6) 0.0490 (16)
H16A −0.6372 0.5125 −0.4057 0.053 (18)*
C17 −0.9439 (9) 0.4716 (4) −0.8264 (6) 0.0455 (16)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Fe1 0.0410 (5) 0.0392 (5) 0.0387 (5) 0.0009 (5) 0.0147 (4) 0.0002 (5)
supporting information
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Acta Cryst. (2004). E60, m1961–m1962
O2 0.060 (3) 0.074 (3) 0.053 (3) −0.021 (3) 0.018 (2) 0.010 (2)
C1 0.058 (5) 0.065 (5) 0.053 (5) 0.031 (4) 0.016 (4) 0.009 (4)
C2 0.041 (4) 0.064 (5) 0.086 (5) 0.001 (4) 0.039 (4) −0.003 (4)
C3 0.079 (5) 0.054 (4) 0.048 (4) 0.002 (4) 0.035 (4) −0.002 (3)
C4 0.096 (6) 0.038 (4) 0.064 (4) −0.017 (4) 0.044 (4) −0.020 (4)
C5 0.084 (5) 0.041 (4) 0.063 (4) 0.018 (4) 0.039 (4) 0.010 (4)
C6 0.054 (4) 0.073 (5) 0.054 (4) 0.004 (4) 0.030 (4) 0.012 (4)
C7 0.036 (4) 0.081 (5) 0.053 (4) 0.005 (4) 0.016 (3) 0.012 (4)
C8 0.043 (4) 0.050 (4) 0.048 (4) 0.010 (3) 0.021 (3) 0.010 (3)
C9 0.058 (5) 0.036 (3) 0.053 (4) 0.001 (3) 0.024 (3) −0.008 (3)
C10 0.079 (5) 0.053 (4) 0.039 (4) 0.022 (4) 0.023 (4) 0.002 (3)
C11 0.040 (4) 0.042 (4) 0.050 (4) 0.009 (3) 0.019 (3) 0.003 (3)
C12 0.047 (4) 0.053 (4) 0.047 (4) −0.011 (3) 0.019 (3) 0.008 (3)
C13 0.039 (4) 0.054 (4) 0.050 (4) −0.012 (3) 0.009 (3) −0.004 (3)
C14 0.039 (4) 0.041 (4) 0.049 (4) 0.005 (3) 0.018 (3) 0.007 (3)
C15 0.044 (4) 0.044 (4) 0.052 (4) −0.009 (3) 0.017 (3) 0.007 (3)
C16 0.046 (4) 0.050 (4) 0.041 (4) −0.013 (3) 0.009 (3) −0.001 (3)
C17 0.040 (4) 0.050 (4) 0.038 (4) 0.006 (3) 0.009 (3) −0.004 (3)
Geometric parameters (Å, º)
Fe1—C1 2.021 (6) C5—H5A 0.9800
Fe1—C9 2.028 (6) C6—C7 1.414 (9)
Fe1—C5 2.031 (6) C6—C10 1.422 (9)
Fe1—C3 2.033 (6) C6—H6A 0.9801
Fe1—C7 2.035 (6) C7—C8 1.427 (8)
Fe1—C2 2.036 (6) C7—H7A 0.9801
Fe1—C6 2.037 (7) C8—C9 1.421 (8)
Fe1—C10 2.042 (6) C8—C11 1.465 (8)
Fe1—C8 2.046 (6) C9—C10 1.409 (8)
Fe1—C4 2.052 (6) C9—H9A 0.9800
O1—C17 1.307 (7) C10—H10A 0.9800
O1—H1B 0.78 (7) C11—C16 1.387 (8)
O2—C17 1.223 (7) C11—C12 1.399 (7)
C1—C5 1.395 (9) C12—C13 1.380 (8)
C1—C2 1.419 (8) C12—H12A 0.9300
C1—H1A 0.9800 C13—C14 1.395 (8)
C2—C3 1.399 (8) C13—H13A 0.9300
C2—H2A 0.9801 C14—C15 1.376 (8)
C3—C4 1.394 (9) C14—C17 1.471 (8)
C3—H3A 0.9801 C15—C16 1.369 (8)
C4—C5 1.419 (9) C15—H15A 0.9300
C4—H4A 0.9799 C16—H16A 0.9300
C1—Fe1—C9 121.9 (3) C3—C4—C5 107.5 (7)
C1—Fe1—C5 40.3 (3) C3—C4—Fe1 69.3 (4)
C9—Fe1—C5 157.7 (3) C5—C4—Fe1 68.9 (4)
C9—Fe1—C3 123.5 (3) C5—C4—H4A 126.2
C5—Fe1—C3 67.9 (3) Fe1—C4—H4A 126.2
C1—Fe1—C7 158.5 (3) C1—C5—C4 107.8 (6)
C9—Fe1—C7 68.4 (3) C1—C5—Fe1 69.5 (4)
C5—Fe1—C7 123.6 (3) C4—C5—Fe1 70.5 (4)
C3—Fe1—C7 124.7 (3) C1—C5—H5A 126.0
C1—Fe1—C2 40.9 (2) C4—C5—H5A 126.2
C9—Fe1—C2 106.9 (3) Fe1—C5—H5A 126.1
C5—Fe1—C2 68.3 (3) C7—C6—C10 107.2 (6)
C3—Fe1—C2 40.2 (2) C7—C6—Fe1 69.6 (4)
C7—Fe1—C2 159.7 (3) C10—C6—Fe1 69.8 (4)
C1—Fe1—C6 121.7 (3) C7—C6—H6A 126.4
C9—Fe1—C6 68.7 (3) C10—C6—H6A 126.5
C5—Fe1—C6 107.1 (3) Fe1—C6—H6A 126.5
C3—Fe1—C6 159.9 (3) C6—C7—C8 109.1 (6)
C7—Fe1—C6 40.6 (2) C6—C7—Fe1 69.8 (4)
C2—Fe1—C6 158.0 (3) C8—C7—Fe1 69.9 (4)
C1—Fe1—C10 106.5 (3) C6—C7—H7A 125.5
C9—Fe1—C10 40.5 (2) C8—C7—H7A 125.4
C5—Fe1—C10 122.1 (3) Fe1—C7—H7A 125.4
C3—Fe1—C10 158.6 (3) C9—C8—C7 106.6 (5)
C7—Fe1—C10 68.1 (3) C9—C8—C11 127.2 (6)
C2—Fe1—C10 122.0 (3) C7—C8—C11 126.2 (6)
C6—Fe1—C10 40.8 (3) C9—C8—Fe1 68.9 (3)
C1—Fe1—C8 158.5 (3) C7—C8—Fe1 69.1 (3)
C9—Fe1—C8 40.8 (2) C11—C8—Fe1 127.4 (4)
C5—Fe1—C8 160.1 (3) C10—C9—C8 108.8 (6)
C3—Fe1—C8 108.7 (3) C10—C9—Fe1 70.3 (4)
C7—Fe1—C8 40.9 (2) C8—C9—Fe1 70.2 (3)
C2—Fe1—C8 122.6 (3) C10—C9—H9A 125.6
C6—Fe1—C8 69.0 (3) C8—C9—H9A 125.6
C10—Fe1—C8 68.5 (2) Fe1—C9—H9A 125.6
C1—Fe1—C4 67.9 (3) C9—C10—C6 108.4 (6)
C9—Fe1—C4 159.6 (3) C9—C10—Fe1 69.2 (3)
C5—Fe1—C4 40.7 (2) C6—C10—Fe1 69.4 (4)
C3—Fe1—C4 39.9 (2) C9—C10—H10A 125.8
C7—Fe1—C4 109.4 (3) C6—C10—H10A 125.8
C2—Fe1—C4 67.7 (3) Fe1—C10—H10A 125.7
C6—Fe1—C4 123.7 (3) C16—C11—C12 117.0 (5)
C10—Fe1—C4 159.2 (3) C16—C11—C8 121.9 (6)
C8—Fe1—C4 124.1 (3) C12—C11—C8 121.1 (5)
C17—O1—H1B 112 (6) C13—C12—C11 121.0 (6)
C5—C1—C2 108.5 (6) C13—C12—H12A 119.5
C5—C1—Fe1 70.2 (4) C11—C12—H12A 119.4
C2—C1—Fe1 70.1 (4) C12—C13—C14 120.9 (6)
C5—C1—H1A 125.7 C12—C13—H13A 119.5
C2—C1—H1A 125.8 C14—C13—H13A 119.6
supporting information
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Acta Cryst. (2004). E60, m1961–m1962
C3—C2—C1 106.9 (6) C15—C14—C17 120.3 (5)
C3—C2—Fe1 69.8 (4) C13—C14—C17 121.9 (6)
C1—C2—Fe1 69.0 (4) C16—C15—C14 121.4 (6)
C3—C2—H2A 126.6 C16—C15—H15A 119.3
C1—C2—H2A 126.4 C14—C15—H15A 119.3
Fe1—C2—H2A 126.5 C15—C16—C11 121.9 (6)
C4—C3—C2 109.3 (6) C15—C16—H16A 119.1
C4—C3—Fe1 70.8 (4) C11—C16—H16A 119.0
C2—C3—Fe1 70.0 (4) O2—C17—O1 123.5 (6)
C4—C3—H3A 125.4 O2—C17—C14 121.5 (6)
C2—C3—H3A 125.3 O1—C17—C14 115.1 (6)
Fe1—C3—H3A 125.3
C9—Fe1—C1—C5 162.0 (4) Fe1—C6—C7—C8 −59.0 (4)
C3—Fe1—C1—C5 −81.4 (4) C10—C6—C7—Fe1 59.9 (5)
C7—Fe1—C1—C5 48.7 (9) C1—Fe1—C7—C6 40.8 (10)
C2—Fe1—C1—C5 −119.2 (6) C9—Fe1—C7—C6 −82.1 (4)
C6—Fe1—C1—C5 78.8 (5) C5—Fe1—C7—C6 76.5 (5)
C10—Fe1—C1—C5 120.6 (4) C3—Fe1—C7—C6 161.3 (4)
C8—Fe1—C1—C5 −166.4 (6) C2—Fe1—C7—C6 −162.4 (7)
C4—Fe1—C1—C5 −38.1 (4) C10—Fe1—C7—C6 −38.4 (4)
C9—Fe1—C1—C2 −78.8 (5) C8—Fe1—C7—C6 −120.4 (6)
C5—Fe1—C1—C2 119.2 (6) C4—Fe1—C7—C6 119.5 (4)
C3—Fe1—C1—C2 37.8 (4) C1—Fe1—C7—C8 161.2 (7)
C7—Fe1—C1—C2 168.0 (7) C9—Fe1—C7—C8 38.2 (4)
C6—Fe1—C1—C2 −162.0 (4) C5—Fe1—C7—C8 −163.1 (4)
C10—Fe1—C1—C2 −120.2 (4) C3—Fe1—C7—C8 −78.3 (5)
C8—Fe1—C1—C2 −47.2 (9) C2—Fe1—C7—C8 −42.0 (10)
C4—Fe1—C1—C2 81.1 (4) C6—Fe1—C7—C8 120.4 (6)
C5—C1—C2—C3 0.3 (7) C10—Fe1—C7—C8 82.0 (4)
Fe1—C1—C2—C3 −59.7 (4) C4—Fe1—C7—C8 −120.1 (4)
C5—C1—C2—Fe1 60.0 (4) C6—C7—C8—C9 −0.1 (7)
C1—Fe1—C2—C3 118.3 (6) Fe1—C7—C8—C9 −59.0 (4)
C9—Fe1—C2—C3 −122.2 (4) C6—C7—C8—C11 −179.3 (6)
C5—Fe1—C2—C3 80.9 (4) Fe1—C7—C8—C11 121.8 (6)
C7—Fe1—C2—C3 −48.9 (10) C6—C7—C8—Fe1 58.9 (5)
C6—Fe1—C2—C3 162.8 (7) C1—Fe1—C8—C9 −42.9 (8)
C10—Fe1—C2—C3 −163.8 (4) C5—Fe1—C8—C9 163.6 (7)
C8—Fe1—C2—C3 −80.3 (5) C3—Fe1—C8—C9 −119.9 (4)
C4—Fe1—C2—C3 36.9 (4) C7—Fe1—C8—C9 118.3 (5)
C9—Fe1—C2—C1 119.5 (4) C2—Fe1—C8—C9 −77.7 (4)
C5—Fe1—C2—C1 −37.4 (4) C6—Fe1—C8—C9 81.3 (4)
C3—Fe1—C2—C1 −118.3 (6) C10—Fe1—C8—C9 37.4 (4)
C7—Fe1—C2—C1 −167.3 (8) C4—Fe1—C8—C9 −161.4 (4)
C6—Fe1—C2—C1 44.5 (9) C1—Fe1—C8—C7 −161.2 (7)
C10—Fe1—C2—C1 77.8 (5) C9—Fe1—C8—C7 −118.3 (5)
C8—Fe1—C2—C1 161.3 (4) C5—Fe1—C8—C7 45.3 (9)
C1—C2—C3—C4 −1.0 (7) C2—Fe1—C8—C7 164.0 (4)
Fe1—C2—C3—C4 −60.1 (5) C6—Fe1—C8—C7 −37.0 (4)
C1—C2—C3—Fe1 59.2 (4) C10—Fe1—C8—C7 −80.9 (4)
C1—Fe1—C3—C4 81.4 (5) C4—Fe1—C8—C7 80.3 (5)
C9—Fe1—C3—C4 −164.0 (4) C1—Fe1—C8—C11 78.5 (9)
C5—Fe1—C3—C4 37.8 (4) C9—Fe1—C8—C11 121.4 (7)
C7—Fe1—C3—C4 −78.6 (5) C5—Fe1—C8—C11 −75.0 (9)
C2—Fe1—C3—C4 119.9 (6) C3—Fe1—C8—C11 1.4 (6)
C6—Fe1—C3—C4 −41.3 (10) C7—Fe1—C8—C11 −120.3 (7)
C10—Fe1—C3—C4 160.1 (7) C2—Fe1—C8—C11 43.7 (7)
C8—Fe1—C3—C4 −121.3 (4) C6—Fe1—C8—C11 −157.3 (6)
C1—Fe1—C3—C2 −38.5 (4) C10—Fe1—C8—C11 158.8 (6)
C9—Fe1—C3—C2 76.0 (5) C4—Fe1—C8—C11 −40.0 (7)
C5—Fe1—C3—C2 −82.1 (4) C7—C8—C9—C10 −0.8 (7)
C7—Fe1—C3—C2 161.5 (4) C11—C8—C9—C10 178.4 (5)
C6—Fe1—C3—C2 −161.2 (7) Fe1—C8—C9—C10 −59.9 (4)
C10—Fe1—C3—C2 40.2 (9) C7—C8—C9—Fe1 59.1 (4)
C8—Fe1—C3—C2 118.8 (4) C11—C8—C9—Fe1 −121.6 (6)
C4—Fe1—C3—C2 −119.9 (6) C1—Fe1—C9—C10 −77.6 (5)
C2—C3—C4—C5 1.2 (8) C5—Fe1—C9—C10 −45.9 (9)
Fe1—C3—C4—C5 −58.4 (4) C3—Fe1—C9—C10 −160.8 (4)
C2—C3—C4—Fe1 59.6 (5) C7—Fe1—C9—C10 81.1 (4)
C1—Fe1—C4—C3 −81.6 (5) C2—Fe1—C9—C10 −119.8 (4)
C9—Fe1—C4—C3 41.2 (10) C6—Fe1—C9—C10 37.3 (4)
C5—Fe1—C4—C3 −119.4 (6) C8—Fe1—C9—C10 119.5 (6)
C7—Fe1—C4—C3 121.2 (4) C4—Fe1—C9—C10 168.8 (8)
C2—Fe1—C4—C3 −37.2 (4) C1—Fe1—C9—C8 162.9 (4)
C6—Fe1—C4—C3 164.2 (4) C5—Fe1—C9—C8 −165.4 (6)
C10—Fe1—C4—C3 −159.6 (7) C3—Fe1—C9—C8 79.8 (4)
C8—Fe1—C4—C3 78.0 (5) C7—Fe1—C9—C8 −38.3 (4)
C1—Fe1—C4—C5 37.8 (4) C2—Fe1—C9—C8 120.7 (4)
C9—Fe1—C4—C5 160.6 (7) C6—Fe1—C9—C8 −82.1 (4)
C3—Fe1—C4—C5 119.4 (6) C10—Fe1—C9—C8 −119.5 (6)
C7—Fe1—C4—C5 −119.4 (4) C4—Fe1—C9—C8 49.3 (10)
C2—Fe1—C4—C5 82.2 (5) C8—C9—C10—C6 1.4 (7)
C6—Fe1—C4—C5 −76.4 (5) Fe1—C9—C10—C6 −58.5 (5)
C10—Fe1—C4—C5 −40.2 (10) C8—C9—C10—Fe1 59.9 (4)
C8—Fe1—C4—C5 −162.6 (4) C7—C6—C10—C9 −1.4 (7)
C2—C1—C5—C4 0.4 (7) Fe1—C6—C10—C9 58.4 (4)
Fe1—C1—C5—C4 60.3 (5) C7—C6—C10—Fe1 −59.8 (5)
C2—C1—C5—Fe1 −59.9 (4) C1—Fe1—C10—C9 120.1 (4)
C3—C4—C5—C1 −1.0 (7) C5—Fe1—C10—C9 161.2 (4)
Fe1—C4—C5—C1 −59.7 (4) C3—Fe1—C10—C9 48.8 (9)
C3—C4—C5—Fe1 58.7 (5) C7—Fe1—C10—C9 −81.9 (4)
C9—Fe1—C5—C1 −43.7 (9) C2—Fe1—C10—C9 78.2 (5)
C3—Fe1—C5—C1 81.5 (4) C6—Fe1—C10—C9 −120.2 (6)
C7—Fe1—C5—C1 −160.7 (4) C8—Fe1—C10—C9 −37.7 (4)
supporting information
sup-7
Acta Cryst. (2004). E60, m1961–m1962
C6—Fe1—C5—C1 −119.2 (4) C1—Fe1—C10—C6 −119.7 (4)
C10—Fe1—C5—C1 −77.1 (5) C9—Fe1—C10—C6 120.2 (6)
C8—Fe1—C5—C1 165.3 (6) C5—Fe1—C10—C6 −78.6 (5)
C4—Fe1—C5—C1 118.6 (6) C3—Fe1—C10—C6 168.9 (6)
C1—Fe1—C5—C4 −118.6 (6) C7—Fe1—C10—C6 38.2 (4)
C9—Fe1—C5—C4 −162.3 (6) C2—Fe1—C10—C6 −161.6 (4)
C3—Fe1—C5—C4 −37.1 (4) C8—Fe1—C10—C6 82.4 (4)
C7—Fe1—C5—C4 80.7 (5) C4—Fe1—C10—C6 −48.9 (10)
C2—Fe1—C5—C4 −80.6 (4) C9—C8—C11—C16 −8.9 (10)
C6—Fe1—C5—C4 122.2 (4) C7—C8—C11—C16 170.1 (6)
C10—Fe1—C5—C4 164.3 (4) Fe1—C8—C11—C16 −99.6 (7)
C8—Fe1—C5—C4 46.7 (9) C9—C8—C11—C12 172.7 (6)
C1—Fe1—C6—C7 −163.6 (4) C7—C8—C11—C12 −8.3 (9)
C9—Fe1—C6—C7 81.2 (4) Fe1—C8—C11—C12 82.0 (7)
C5—Fe1—C6—C7 −122.1 (4) C16—C11—C12—C13 −0.1 (9)
C3—Fe1—C6—C7 −50.0 (10) C8—C11—C12—C13 178.4 (6)
C2—Fe1—C6—C7 163.7 (7) C11—C12—C13—C14 1.8 (10)
C10—Fe1—C6—C7 118.2 (6) C12—C13—C14—C15 −2.6 (9)
C8—Fe1—C6—C7 37.3 (4) C12—C13—C14—C17 178.5 (6)
C4—Fe1—C6—C7 −80.6 (5) C13—C14—C15—C16 1.9 (9)
C1—Fe1—C6—C10 78.2 (5) C17—C14—C15—C16 −179.2 (6)
C9—Fe1—C6—C10 −37.0 (4) C14—C15—C16—C11 −0.3 (10)
C5—Fe1—C6—C10 119.7 (4) C12—C11—C16—C15 −0.6 (9)
C3—Fe1—C6—C10 −168.2 (7) C8—C11—C16—C15 −179.1 (6)
C7—Fe1—C6—C10 −118.2 (6) C15—C14—C17—O2 5.0 (9)
C2—Fe1—C6—C10 45.5 (9) C13—C14—C17—O2 −176.1 (6)
C8—Fe1—C6—C10 −81.0 (4) C15—C14—C17—O1 −175.1 (6)
C4—Fe1—C6—C10 161.2 (4) C13—C14—C17—O1 3.8 (9)
C10—C6—C7—C8 0.9 (7)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H1B···O2i 0.81 (6) 1.86 (6) 2.646 (6) 162 (7)
