Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
A hexacarbonyldicobalt(0) complex
of a `magazine-rack' molecule,
[(
g
2-C
32
H
20)Co
2(CO)
6]CH
2Cl
2Akihiro Orita,aLasheng Jiang,a
Fangguo Ye,aNobuyuki Imai,a
Haruo Akashib and Junzo
Oteraa*
aDepartment of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan, andbResearch Institute of Natural Sciences, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 113 K
Mean(C±C) = 0.002 AÊ
Rfactor = 0.026
wRfactor = 0.089
Data-to-parameter ratio = 16.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography
The title compound, -pentacyclo[26.4.0.09,14.017,22.025,30
]- dotriaconta-1,3,5,9,11,13,15,17,19,21,25,27,29,31-tetradecaene-7,24-diyne-bis(tricarbonylcobalt) dichloromethane solvate, [Co2(2-C32H20)(CO)6]CH2Cl2, has been prepared by
treat-ment of a dehydrobenzoannulene with octacarbonyldicobalt. This cobalt complex is chiral in the solid state and exhibits alternate arrays ofP- andM-conformations.
Comment
Various types of dehydroannulenes (Diederich, 1995; Tobeet al., 1996) and their benzannelated analogs (Iyodaet al., 2001; Palmeret al., 2001) have been synthesized thus far. Much of the interest can be attributed to the recognition that such categories of compounds can potentially serve as versatile precursors for carbon-rich molecular (Tobeet al., 1998, 2001) and polymeric systems (Dosaet al., 1999). For example, it has been reported that heating of a dehydrobenzoannulene at 518 K leads to the formation of a `graphitic onion' (Boeseet al., 1997). Furthermore, it has been reported that powdered cobalt metal accelerates the growth of single-wall carbon nanotubes from vaporized carbon in an arc generator (Bethune et al., 1993). From these experimental results we expected that cobalt-coordinating dehydrobenzoannulenes might be promising precursors for carbon nanotubes, because they are easy to handle due to their stability in air, and might be transformed to carbon nanotubes at a lower temperature than those hitherto reported. Thus, as part of our project to explore -conjugated cyclophane derivatives having unique structural and electronic features (Oritaet al., 2002; Anet al., 2002), we tackled the preparation of cobalt-coordinating
-conjugated cyclophanes. We envisioned that the title compound, (I), could be obtained by the reaction of Co2(CO)8
with a `magazine-rack' type molecule, such as a cyclophane having alternating phenylene±ethynylene, as well as phenyl-ene±ethenylene arrays, (II) (Oritaet al., 2002).
As shown in Fig. 1, the dicobalt complex, (I), has a linear uncoordinated acetylene moiety and a bent acetylene
two phenylenes are connected by acetylene with a dihedral angle of 23.0, in the cobalt complex, (I), the corresponding
dihedral angle between the C11ÐC16 and C19ÐC24 planes
was found to be 30.8 (1). It has been reported that, in the
solid state, the-conjugated cyclophane (II) adopts a concave structure like a magazine-rack, with alternate arrays of theP -and M-conformations. Upon formation of complex (I), this concave feature was lost, but (I) is still chiral and retains alternate arrays of the P- and M-conformers with respect to the uncoordinated diphenylacetylene moiety in the crystal; this is illustrated in Fig. 2.
Experimental
Preparation of (I): to a ¯ame-dried ¯ask were added (II) (100.1 mg, 0.5 mmol), Co2(CO)8(512.9 mg, 0.5 mmol) and CH2Cl2(10 ml). The
mixture was stirred for 12 h at room temperature in the dark. After evaporation, hexane was added to the residual black solids and the mixture ®ltered through a thin layer of silica gel. After evaporation of the resulting ®ltrate, dark-purple crystals were obtained in 50±60% yield.
Crystal data
[Co2(C32H20)(CO)6]CH2Cl2 Mr= 775.37
Monoclinic,P21=c a= 13.0348 (3) AÊ
b= 10.9999 (3) AÊ
c= 23.8599 (5) AÊ
= 94.584 (1)
V= 3410.1 (1) AÊ3 Z= 4
Dx= 1.510 Mg mÿ3
MoKradiation Cell parameters from 9554
re¯ections
= 2.9±27.5
= 1.18 mmÿ1 T= 113.1 K Plate, dark purple 0.300.150.10 mm
Data collection
Rigaku R-AXIS-IV diffractometer
!scans
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)
Tmin= 0.719,Tmax= 0.889
18 119 measured re¯ections 7873 independent re¯ections
6460 re¯ections withF2> 2(F2) Rint= 0.019
max= 27.5 h=ÿ16!16
k=ÿ14!14
l=ÿ21!30
Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.026 wR(F2) = 0.089 S= 0.90 7523 re¯ections 464 parameters
All H-atom parameters re®ned
w= 1/[0.002Fo2+2(Fo)]/(4Fo2)
(/)max< 0.001 max= 0.44 e AÊÿ3 min=ÿ0.72 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
Co2ÐCo1 2.4524 (3) Co1ÐC2 1.9731 (13) Co1ÐC1 1.9798 (14) C2ÐC1 1.346 (2)
C2ÐC3 1.4707 (19) C16ÐC17 1.440 (2) C17ÐC18 1.201 (2) C1ÐC2ÐC3 147.39 (14)
C16ÐC17ÐC18 178.10 (17) C2ÐC3ÐC4 118.80 (13) C3ÐC2ÐC1ÐC32 ÿ2.8 (6)
Data collection: PROCESS-AUTO (Rigaku, 1998); cell re®ne-ment:PROCESS-AUTO; data reduction:TEXSAN(Rigaku, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1998); soft-ware used to prepare material for publication: CrystalStructure (Molecular Structure Corporation & Rigaku, 2001).
Figure 1
The molecular structure of the title complex. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Financial support from the New Energy and Industrial Technology Development Organization (NEDO) of Japan for an Industrial Technology Research Grant Program (01B68006d) to AO is gratefully acknowledged.
References
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).J. Appl. Cryst.32, 115±119.
An, D. L., Nakano, T., Orita, A. & Otera, J. (2002).Angew. Chem. Int. Ed.41, 171.
Bethune, D. S., Kiang, C. H., de Vries, M. S., Gorman, G., Savoy, R., Vazquez, J. & Beyers, R. (1993).Nature (London),363, 605±607.
Boese, R., Matzger, A. J. & Vollhardt, K. P. C. (1997).J. Am. Chem. Soc.119, 2052±2053.
Diederich, F. (1995).Modern Acetylene Chemistry, edited by P. J. Stang and F. Diederich. VCH: Weinheim.
Dosa, P. I., Erben, C., Iyer, V. S., Vollhardt, K. P. C. & Wasser, I. M. (1999).J. Am. Chem. Soc.121, 10430±10431.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565±565.
Higashi, T. (1995).ABSCOR.Rigaku Corporation, Tokyo, Japan.
Iyoda, M., Horino, T., Takahashi, F., Hasegawa, M., Yoshida, M. & Kuwatani, Y. (2001).Tetrahedron Lett.42, 6883±6886.
Molecular Structure Corporation & Rigaku (2001).CrystalStructure. Version 2.00. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA, and Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan.
Orita, A., Jiang, L., Tsuruta, M. & Otera, J. (2002).Chem. Lett.pp. 136±137. Palmer, G. J., Parkin, S. R. & Anthony, J. E. (2001).Angew. Chem. Int. Ed.40,
2509±2512.
Rigaku (1998).PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku (1999).TEXSAN.Version 1.10. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Tobe, Y., Matsumoto, H., Naemura, K., Achiba, Y. & Wakabayashi, T. (1996).
Angew. Chem. Int. Ed. Engl.35, 1800±1802.
Tobe, Y., Nakagawa, N., Kishi, J., Sonoda, M., Naemura, K., Wakabayashi, T., Shida, T. & Achiba, Y. (2001).Tetrahedron,57, 3629±3636.
supporting information
Acta Cryst. (2002). E58, m681–m683 [https://doi.org/10.1107/S1600536802019281]
A hexacarbonyldicobalt(0) complex of a `magazine-rack
′
molecule, [(
η
2-C
32H
20)Co
2(CO)
6]
·
CH
2Cl
2Akihiro Orita, Lasheng Jiang, Fangguo Ye, Nobuyuki Imai, Haruo Akashi and Junzo Otera
µ-pentacyclo[26.4.0.09,14.017,22.025,30]dotriaconta-
1,3,5,9,11,13,15,17,19,21,25,27,29,31-tetradecaene-7,24-diyne- bis(tricarbonylcobalt) dichloromethane solvate
Crystal data
[Co2(C32H20)(CO)6]·CH2Cl2
Mr = 775.37 Monoclinic, P21/c
a = 13.0348 (3) Å b = 10.9999 (3) Å c = 23.8599 (5) Å β = 94.584 (1)° V = 3410.1 (1) Å3
Z = 4
Dx = 1.510 Mg m−3
Mo Kα radiation, λ = 0.7107 Å Cell parameters from 9554 reflections θ = 2.9–27.5°
µ = 1.18 mm−1
T = 113 K Plate, dark purple 0.30 × 0.15 × 0.10 mm
Data collection Rigaku R-AXIS-IV
diffractometer
Detector resolution: 10.00 pixels mm-1
ω scans
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) Tmin = 0.719, Tmax = 0.889
18119 measured reflections
7873 independent reflections 6460 reflections with F2 > 2σ(F2)
Rint = 0.019
θmax = 27.5°
h = −16→16 k = −14→14 l = −21→30
Refinement Refinement on F2
R[F2 > 2σ(F2)] = 0.026
wR(F2) = 0.089
S = 0.90 7523 reflections 464 parameters
All H-atom parameters refined w = 1/[0.002Fo2 + σ2(Fo)]/(4Fo2)
(Δ/σ)max < 0.001
Δρmax = 0.44 e Å−3
Δρmin = −0.72 e Å−3
Special details
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are
based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
H10 0.6538 (1) 0.7764 (1) 0.56466 (7) 0.025 (1)* H9 0.5030 (1) 0.8931 (1) 0.53379 (7) 0.027 (1)* H8 0.3963 (1) 0.8308 (1) 0.45691 (7) 0.026 (1)* H7 0.4283 (1) 0.6481 (1) 0.40815 (7) 0.023 (1)* H3 0.7280 (1) 0.8107 (1) 0.30806 (7) 0.019 (1)* H4 0.6570 (1) 0.6946 (1) 0.38103 (6) 0.018 (1)* H6 0.5571 (1) 0.4194 (1) 0.45497 (6) 0.017 (1)* H5 0.6247 (1) 0.3674 (1) 0.37811 (6) 0.013 (1)* H2 0.7997 (1) 0.7166 (1) 0.23412 (6) 0.018 (1)* H1 0.7906 (1) 0.4991 (1) 0.22719 (6) 0.016 (1)* H16 0.8358 (1) 0.3629 (1) 0.37522 (6) 0.015 (1)* H15 0.9160 (1) 0.4704 (1) 0.44013 (6) 0.018 (1)* H11 0.8901 (1) 0.4852 (2) 0.63685 (7) 0.029 (1)* H12 1.0242 (1) 0.3542 (2) 0.66393 (7) 0.031 (1)* H13 1.1046 (1) 0.2315 (2) 0.59223 (8) 0.027 (1)* H14 1.0454 (1) 0.2536 (1) 0.50009 (7) 0.023 (1)* H17 0.8351 (1) 0.1683 (1) 0.49877 (6) 0.019 (1)* H18 0.7596 (1) −0.0328 (1) 0.49999 (7) 0.021 (1)* H19 0.6646 (1) −0.1016 (1) 0.42010 (7) 0.019 (1)* H20 0.6484 (1) 0.0192 (1) 0.33641 (6) 0.016 (1)* H21 0.9908 (1) 0.0660 (2) 0.41726 (8) 0.037 (1)* H22 1.0852 (1) −0.0363 (2) 0.41754 (8) 0.038 (1)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C26 0.0116 (6) 0.0124 (7) 0.0142 (7) −0.0014 (5) −0.0008 (5) 0.0028 (6) C6 0.0200 (8) 0.0089 (7) 0.0170 (8) −0.0008 (5) 0.0036 (6) −0.0002 (5) C19 0.0138 (7) 0.0239 (8) 0.0159 (7) −0.0077 (6) −0.0003 (6) 0.0054 (6) C7 0.0180 (7) 0.0111 (7) 0.0142 (7) 0.0000 (6) 0.0041 (6) −0.0020 (5) C16 0.0162 (7) 0.0194 (7) 0.0143 (7) −0.0028 (6) 0.0073 (6) 0.0002 (6) C20 0.0216 (8) 0.038 (1) 0.0136 (7) −0.0088 (7) 0.0019 (6) 0.0055 (7) C17 0.0187 (7) 0.0241 (8) 0.0144 (7) −0.0053 (6) 0.0040 (6) −0.0025 (6) C8 0.0110 (6) 0.0112 (6) 0.0102 (6) 0.0001 (5) 0.0009 (5) 0.0004 (5) C25 0.0149 (7) 0.0132 (7) 0.0156 (7) −0.0043 (6) −0.0019 (5) 0.0027 (6) C34 0.0129 (7) 0.0124 (7) 0.0168 (7) 0.0009 (5) 0.0026 (6) −0.0020 (6) C18 0.0175 (7) 0.0242 (8) 0.0156 (7) −0.0063 (6) 0.0035 (6) −0.0004 (6) C11 0.0172 (7) 0.0160 (7) 0.0118 (7) −0.0009 (6) 0.0070 (5) 0.0007 (6) C4 0.0157 (7) 0.0112 (7) 0.0117 (7) 0.0004 (6) 0.0033 (5) −0.0004 (5) C10 0.0149 (7) 0.0141 (7) 0.0123 (7) −0.0008 (5) 0.0025 (5) 0.0020 (5) C14 0.0299 (9) 0.0169 (7) 0.0213 (8) −0.0024 (7) 0.0120 (7) −0.0036 (7) C32 0.0097 (6) 0.0103 (6) 0.0107 (6) 0.0016 (5) 0.0019 (5) 0.0002 (5) C29 0.0217 (8) 0.0153 (7) 0.0148 (7) −0.0032 (6) −0.0008 (6) 0.0057 (6) C15 0.0249 (8) 0.0201 (8) 0.0177 (8) −0.0069 (7) 0.0082 (7) −0.0039 (6) C13 0.0261 (9) 0.0203 (8) 0.0183 (8) 0.0066 (7) 0.0078 (7) 0.0029 (6) C23 0.0202 (8) 0.0158 (7) 0.0224 (8) −0.0051 (6) −0.0075 (6) 0.0019 (6) C21 0.0230 (8) 0.040 (1) 0.0153 (8) −0.0123 (8) −0.0055 (6) 0.0125 (7) C28 0.0195 (7) 0.0151 (7) 0.0127 (7) −0.0041 (6) −0.0036 (6) 0.0017 (6) C3 0.0113 (6) 0.0088 (6) 0.0105 (6) −0.0004 (5) 0.0002 (5) −0.0006 (5) C31 0.0152 (7) 0.0109 (7) 0.0134 (7) −0.0012 (5) 0.0012 (5) −0.0017 (6) C12 0.0214 (8) 0.0215 (8) 0.0134 (7) 0.0013 (6) 0.0053 (6) 0.0006 (6) C22 0.0215 (8) 0.0225 (8) 0.0255 (9) −0.0082 (7) −0.0103 (7) 0.0098 (7) C39 0.0277 (9) 0.043 (1) 0.0224 (9) 0.0016 (9) 0.0036 (7) −0.0016 (8)
Geometric parameters (Å, º)
Co2—Co1 2.4524 (3) C6—C7 1.392 (2)
Co2—C36 1.8136 (16) C6—H3 0.960 (2)
Co2—C38 1.8305 (16) C19—C20 1.406 (2)
Co2—C2 1.9859 (14) C19—C18 1.434 (2)
Co2—C37 1.8120 (16) C7—C8 1.403 (2)
Co2—C1 1.9773 (15) C7—H4 0.989 (2)
Co1—C2 1.9731 (13) C16—C17 1.440 (2)
Co1—C35 1.8241 (15) C16—C11 1.413 (2)
Co1—C33 1.8081 (17) C16—C15 1.407 (2)
Co1—C1 1.9798 (14) C20—C21 1.388 (3)
Co1—C34 1.8193 (16) C20—H11 0.970 (3)
Cl2—C39 1.761 (2) C17—C18 1.201 (2)
Cl1—C39 1.758 (2) C8—C3 1.4239 (19)
O4—C36 1.130 (2) C25—H15 0.952 (2)
O3—C35 1.1382 (19) C11—C10 1.489 (2)
O6—C38 1.131 (2) C11—C12 1.396 (2)
O5—C37 1.1356 (19) C4—C3 1.4022 (19)
O1—C33 1.135 (2) C10—H6 0.983 (2)
C2—C1 1.346 (2) C14—C15 1.384 (3)
C2—C3 1.4707 (19) C14—C13 1.392 (3)
C5—C6 1.389 (2) C14—H9 0.942 (3)
C5—C4 1.389 (2) C32—C31 1.4072 (19)
C5—H2 0.985 (2) C29—C28 1.389 (2)
C9—C8 1.4691 (19) C29—H18 0.982 (2)
C9—C10 1.336 (2) C15—H10 0.986 (2)
C9—H5 0.974 (2) C13—C12 1.393 (2)
C24—C19 1.411 (2) C13—H8 0.949 (2)
C24—C25 1.484 (2) C23—C22 1.400 (2)
C24—C23 1.400 (2) C23—H14 0.983 (2)
C30—C29 1.393 (2) C21—C22 1.382 (3)
C30—C31 1.381 (2) C21—H12 0.944 (3)
C30—H19 0.950 (2) C28—H17 0.970 (3)
C1—C32 1.4703 (19) C31—H20 0.974 (3)
C27—C26 1.4681 (19) C12—H7 1.014 (3)
C27—C32 1.423 (2) C22—H13 0.985 (3)
C27—C28 1.407 (2) C39—H21 0.912 (3)
C26—C25 1.339 (2) C39—H22 0.996 (3)
C26—H16 0.979 (2)
Co2···Co1 2.4524 (3) C19···C17 2.635 (2)
Co2···O4 2.9426 (11) C19···C25 2.500 (2)
Co2···O6 2.9600 (12) C19···C25iii 3.496 (2)
Co2···O5 2.9469 (11) C19···C18 1.434 (2)
Co2···C36 1.8136 (16) C19···C23 2.420 (2)
Co2···C38 1.8305 (16) C19···C21 2.428 (2)
Co2···C2 1.9859 (14) C19···C22 2.801 (2)
Co2···C35 3.2875 (15) C19···H15 2.799 (2)
Co2···C37 1.8120 (16) C19···H15iii 2.844 (2)
Co2···C1 1.9773 (15) C19···H11 2.053 (2)
Co2···C34 3.1947 (15) C19···H12 3.261 (2)
Co2···C32 3.1617 (14) C19···H14 3.304 (2)
Co2···C3 3.1577 (14) C19···H17 3.282 (2)
Co2···C31 3.5291 (15) C7···C8 1.403 (2)
Co2···H5 3.3028 (15) C7···C11 3.173 (2)
Co2···H20 3.0307 (15) C7···C4 2.768 (2)
Co1···O3 2.9613 (11) C7···C10 3.107 (2)
Co1···O2 2.9602 (11) C7···C3 2.423 (2)
Co1···O1 2.9423 (12) C7···C12 3.581 (2)
Co1···C38 3.3672 (15) C7···H3 2.067 (2)
Co1···C2 1.9731 (13) C7···H4 0.989
Co1···C35 1.8241 (15) C7···H5 3.344 (2)
Co1···C33 1.8081 (17) C7···H2 3.288 (2)
Co1···C37 3.1397 (15) C7···H13iii 3.301 (2)
Co1···C1 1.9798 (14) C7···H19x 3.209 (2)
Co1···C4 3.5079 (15) C16···C18 2.641 (2)
Co1···C32 3.1584 (14) C16···C11 1.413 (2)
Co1···C3 3.1575 (14) C16···C10 2.511 (2)
Co1···H1 3.0475 (15) C16···C10vi 3.593 (2)
Co1···H16 3.4868 (15) C16···C14 2.422 (2)
Cl2···Cl1 2.9142 (7) C16···C15 1.407 (2)
Cl2···O3 3.1917 (14) C16···C13 2.797 (2)
Cl2···O1i 3.4021 (14) C16···C12 2.418 (2)
Cl2···C35 3.3231 (16) C16···H10 2.027 (2)
Cl2···C33i 3.5942 (15) C16···H9 3.270 (2)
Cl2···C39 1.761 (2) C16···H7 3.344 (2)
Cl2···H1i 3.2287 (15) C16···H4 3.015 (2)
Cl2···H13ii 3.3139 (17) C16···H6 2.908 (2)
Cl2···H21 2.204 (2) C16···H6vi 2.812 (2)
Cl2···H22 2.256 (2) C16···H19x 3.442 (2)
Cl1···O1 3.5731 (14) C20···C17 3.574 (2)
Cl1···C39 1.758 (2) C20···C25iii 3.526 (2)
Cl1···H10iii 2.9498 (18) C20···C34xi 3.411 (2)
Cl1···H2i 3.3902 (16) C20···C18 2.467 (2)
Cl1···H14 3.009 (2) C20···C23 2.778 (3)
Cl1···H18ii 3.0224 (17) C20···C21 1.388 (3)
Cl1···H21 2.181 (2) C20···C22 2.401 (3)
Cl1···H22 2.236 (2) C20···H15iii 2.767 (2)
O4···O6iv 3.4258 (17) C20···H11 0.970
O4···O5v 3.0962 (16) C20···H12 2.004 (2)
O4···C36 1.130 (2) C20···H13 3.328 (3)
O4···C5iv 3.370 (2) C17···C25 3.581 (2)
O4···C15vi 3.368 (2) C17···C18 1.201 (2)
O4···H10vi 2.821 (2) C17···C11 2.467 (2)
O4···H9vi 3.444 (2) C17···C10 2.869 (2)
O4···H5 3.1007 (19) C17···C15 2.475 (2)
O4···H2iv 3.351 (2) C17···H10 2.578 (2)
O4···H20 3.4862 (19) C17···H6 3.099 (2)
O3···O5 3.2009 (17) C17···H15 3.550 (2)
O3···O1i 3.0304 (16) C17···H11 3.529 (2)
O3···C5vii 3.3427 (18) C8···C11 3.276 (2)
O3···C35 1.1382 (19) C8···C4 2.438 (2)
O3···C37 3.3053 (19) C8···C10 2.553 (2)
O3···C6vii 3.3474 (19) C8···C3 1.4239 (19)
O3···C20viii 3.599 (2) C8···H3 3.315 (2)
O3···H3vii 2.6869 (19) C8···H4 2.057 (2)
O3···H2vii 2.6657 (18) C8···H6 3.381 (2)
O3···H11viii 2.696 (2) C8···H5 2.0707 (19)
O3···H20 3.4339 (18) C8···H1 3.291 (2)
O6···O5v 3.4787 (18) C8···H16 2.859 (2)
O6···O2 3.4687 (17) C25···C18 2.861 (2)
O6···C36v 3.5886 (19) C25···C23 2.514 (2)
O6···C37v 3.5615 (19) C25···H16 1.948 (2)
O6···C30v 3.554 (2) C25···H15 0.952
O6···C34 3.5147 (19) C25···H14 2.678 (2)
O6···C13iv 3.531 (2) C25···H17 2.841 (2)
O6···C31v 3.2726 (19) C34···C4 3.485 (2)
O6···C12iv 3.597 (2) C34···C21viii 3.543 (2)
O6···H8iv 3.316 (2) C34···H7iv 3.515 (2)
O6···H7iv 3.435 (2) C34···H1 2.703 (2)
O6···H3iv 3.588 (2) C34···H11viii 3.435 (2)
O6···H4iv 3.482 (2) C34···H12viii 3.569 (2)
O6···H19v 3.147 (2) C34···H22ix 3.516 (2)
O6···H20v 2.6157 (18) C18···C11 3.545 (2)
O5···C36iv 3.0144 (18) C18···C10 3.579 (2)
O5···C38iv 3.3067 (19) C18···C15 3.585 (3)
O5···C35 3.2086 (19) C18···H10 3.477 (2)
O5···C9iv 3.2411 (19) C18···H15 2.958 (2)
O5···C37 1.1356 (19) C18···H11 2.627 (2)
O5···C8iv 3.3448 (19) C18···H14iii 3.446 (2)
O5···H7iv 3.273 (2) C11···C10 1.489 (2)
O5···H3vii 3.585 (2) C11···C10vi 3.536 (2)
O5···H5iv 3.3809 (18) C11···C14 2.806 (2)
O5···H20 3.212 (2) C11···C15 2.438 (2)
O2···C38 3.4038 (18) C11···C13 2.428 (2)
O2···C20viii 3.446 (2) C11···C12 1.396 (2)
O2···C34 1.142 (2) C11···H10 3.293 (2)
O2···C13iv 3.586 (2) C11···H8 3.293 (2)
O2···C39ix 3.479 (2) C11···H7 2.102 (2)
O2···H8iv 2.834 (2) C11···H4 2.448 (2)
O2···H7iv 3.253 (2) C11···H6 2.080 (2)
O2···H1 3.0660 (19) C11···H6vi 2.747 (2)
O2···H17viii 3.2743 (19) C11···H5 3.380 (2)
O2···H22ix 2.761 (2) C11···H19x 3.584 (2)
O1···C33 1.135 (2) C4···C3 1.4022 (19)
O1···H2i 2.9197 (19) C4···H3 3.254 (2)
O1···H1 3.5710 (19) C4···H2 2.089 (2)
O1···H16 3.1903 (19) C4···H1 0.955
O1···H11iii 3.240 (2) C4···H16 3.509 (2)
O1···H12viii 3.420 (2) C4···H12iii 3.463 (2)
C36···C38 2.854 (2) C10···C12 2.511 (2)
C36···C2 3.063 (2) C10···H7 2.710 (2)
C36···C9 3.544 (2) C10···H4 2.810 (2)
C36···C37 2.714 (2) C10···H6 0.983
C36···C1 2.830 (2) C10···H6vi 3.516 (3)
C36···C32 3.405 (2) C10···H5 1.953 (2)
C36···C31 3.460 (2) C14···C15 1.384 (3)
C36···H5 2.832 (2) C14···C13 1.392 (3)
C36···H20 3.034 (2) C14···C12 2.409 (2)
C38···C37 2.907 (2) C14···H9 0.942
C38···C1 3.523 (2) C14···H9xii 3.330 (3)
C38···C34 3.098 (2) C14···H8 2.023 (3)
C38···C3 3.331 (2) C14···H7 3.315 (2)
C38···H7iv 3.328 (2) C14···H6vi 2.962 (2)
C38···H4iv 3.586 (2) C14···H18x 3.546 (2)
C38···H1 3.589 (2) C14···H19x 3.153 (2)
C38···H20v 3.390 (2) C32···C29 2.811 (2)
C2···C35 3.543 (2) C32···C28 2.426 (2)
C2···C9 2.9233 (19) C32···C31 1.4072 (19)
C2···C33 2.850 (2) C32···H5 2.7314 (19)
C2···C37 3.598 (2) C32···H16 2.604 (2)
C2···C1 1.346 (2) C32···H17 3.297 (2)
C2···C27 3.430 (2) C32···H19 3.284 (2)
C2···C26 3.278 (2) C32···H20 2.010 (2)
C2···C8 2.5309 (19) C32···H21 3.597 (2)
C2···C34 3.052 (2) C29···C28 1.389 (2)
C2···C4 2.473 (2) C29···C31 2.399 (2)
C2···C32 2.698 (2) C29···H9vi 3.470 (2)
C2···C3 1.4707 (19) C29···H8vi 3.209 (2)
C2···H5 2.4864 (19) C29···H17 2.046 (2)
C2···H1 2.598 (2) C29···H18 0.982
C2···H16 2.519 (2) C29···H19 2.054 (2)
C5···C6 1.389 (2) C29···H20 3.305 (2)
C5···C7 2.409 (2) C29···H21 3.439 (2)
C5···C8 2.826 (2) C29···H22ii 3.331 (3)
C5···C4 1.389 (2) C15···C13 2.407 (3)
C5···C3 2.436 (2) C15···C12 2.782 (2)
C5···H3 2.025 (2) C15···H10 0.986
C5···H4 3.303 (2) C15···H9 2.023 (2)
C5···H2 0.985 C15···H8 3.252 (3)
C5···H1 2.046 (2) C15···H6vi 2.922 (2)
C5···H12iii 3.142 (2) C15···H18x 3.182 (2)
C35···C33 2.810 (2) C15···H19x 3.221 (2)
C35···C37 2.933 (2) C13···C12 1.393 (2)
C35···C1 2.896 (2) C13···H10 3.325 (3)
C35···C20viii 3.492 (2) C13···H9 2.036 (2)
C35···C34 2.908 (2) C13···H9xii 3.596 (2)
C35···C32 3.470 (2) C13···H8 0.949
C35···H3vii 3.422 (2) C13···H7 2.075 (2)
C35···H11viii 2.771 (2) C13···H6vi 2.908 (2)
C35···H12viii 3.580 (2) C13···H19x 3.290 (2)
C35···H20 3.282 (2) C23···C21 2.408 (3)
C9···C1 3.3023 (19) C23···C28 3.481 (2)
C9···C27 3.578 (2) C23···C22 1.400 (2)
C9···C26 3.238 (2) C23···H15 3.044 (2)
C9···C7 2.520 (2) C23···H15iii 2.839 (2)
C9···C8 1.4691 (19) C23···H13 2.008 (2)
C9···C11 2.571 (2) C23···H14 0.983
C9···C10 1.336 (2) C23···H17 2.703 (2)
C9···C3 2.498 (2) C23···H22ii 3.385 (3)
C9···C12 3.421 (2) C21···C22 1.382 (3)
C9···H7 3.400 (2) C21···H15iii 2.751 (2)
C9···H4 2.679 (2) C21···H11 2.060 (3)
C9···H6 1.977 (2) C21···H12 0.944
C9···H5 0.974 C21···H13 2.122 (3)
C9···H16 2.967 (2) C21···H14 3.291 (3)
C33···C1 2.950 (2) C28···C31 2.765 (2)
C33···C34 2.787 (2) C28···H8vi 3.326 (2)
C33···C4 3.562 (2) C28···H16 3.357 (2)
C33···C3 3.509 (2) C28···H14 3.483 (2)
C33···H1 3.079 (2) C28···H17 0.970
C33···H16 3.002 (2) C28···H18 2.106 (2)
C33···H12viii 3.274 (2) C28···H19 3.272 (2)
C24···C24iii 3.526 (3) C28···H21 2.894 (2)
C24···C27 3.307 (2) C28···H22ii 3.250 (2)
C24···C26 2.582 (2) C3···H4 3.307 (2)
C24···C19 1.411 (2) C3···H5 2.595 (2)
C24···C20 2.433 (2) C3···H2 3.337 (2)
C24···C17 3.544 (2) C3···H1 2.0336 (19)
C24···C25 1.484 (2) C3···H16 2.628 (2)
C24···C25iii 3.571 (2) C31···H9vi 3.571 (2)
C24···C18 2.463 (2) C31···H3vii 3.037 (2)
C24···C23 1.400 (2) C31···H18 3.258 (2)
C24···C21 2.808 (2) C31···H19 2.022 (2)
C24···C28 3.221 (2) C31···H20 0.974
C24···C22 2.437 (2) C12···H9 3.261 (2)
C24···H16 3.380 (2) C12···H8 2.058 (2)
C24···H15 2.034 (2) C12···H7 1.014
C24···H15iii 2.875 (2) C12···H4 2.822 (2)
C24···H11 3.299 (2) C12···H6 3.025 (2)
C24···H13 3.278 (2) C12···H6vi 2.792 (2)
C24···H14 2.064 (2) C12···H19x 3.498 (2)
C24···H17 2.523 (2) C22···H15iii 2.795 (2)
C37···C1 3.125 (2) C22···H11 3.280 (3)
C37···H7iv 3.272 (2) C22···H12 2.050 (3)
C37···H20 2.796 (2) C22···H13 0.985
C30···C27 2.823 (2) C22···H14 2.072 (3)
C30···C32 2.436 (2) C22···H17 3.549 (2)
C30···C29 1.393 (2) C22···H22ii 3.236 (3)
C30···C28 2.406 (2) C39···H13ii 3.514 (3)
C30···C31 1.381 (2) C39···H14 3.395 (3)
C30···H9vi 3.253 (2) C39···H17ii 3.541 (3)
C30···H3vii 3.274 (2) C39···H18ii 3.343 (3)
C30···H13ii 3.475 (2) C39···H22 0.996
C30···H17 3.277 (2) H10···H9 2.412 (3)
C30···H18 2.024 (2) H10···H6vi 3.494 (2)
C30···H19 0.950 H10···H18x 3.005 (2)
C30···H20 2.092 (2) H9···H9xii 2.849 (3)
C1···C27 2.544 (2) H9···H8 2.316 (3)
C1···C26 2.944 (2) H9···H8xii 3.310 (2)
C1···C8 3.443 (2) H9···H6vi 3.541 (2)
C1···C34 3.593 (2) H9···H18x 3.597 (2)
C1···C32 1.4703 (19) H9···H19x 3.566 (2)
C1···C3 2.7033 (19) H9···H19vi 3.410 (2)
C1···C31 2.466 (2) H8···H7 2.376 (2)
C1···H5 2.5340 (19) H8···H6vi 3.487 (2)
C1···H16 2.522 (2) H8···H17vi 3.274 (2)
C1···H20 2.524 (2) H8···H18vi 3.234 (2)
C27···C26 1.4681 (19) H7···H4 3.141 (2)
C27···C25 2.558 (2) H7···H6 3.177 (2)
C27···C32 1.423 (2) H7···H6vi 3.340 (2)
C27···C29 2.444 (2) H3···H4 2.404 (2)
C27···C28 1.407 (2) H3···H2 2.307 (2)
C27···C31 2.437 (2) H3···H13iii 3.132 (2)
C27···H5 2.935 (2) H3···H19x 3.019 (2)
C27···H16 2.082 (2) H3···H20x 2.628 (2)
C27···H15 3.357 (2) H4···H13iii 3.227 (2)
C27···H17 2.055 (2) H4···H19x 2.427 (2)
C27···H18 3.352 (2) H6···H6vi 3.238 (3)
C27···H20 3.280 (2) H6···H5 2.174 (2)
C27···H21 2.970 (2) H5···H16 2.7582 (19)
C26···C19 3.596 (2) H2···H1 2.400 (2)
C26···C8 3.500 (2) H2···H12iii 3.302 (2)
C26···C25 1.339 (2) H16···H15 2.152 (2)
C26···C32 2.494 (2) H15···H15iii 3.519 (3)
C26···C23 3.389 (2) H15···H11iii 3.278 (2)
C26···C28 2.523 (2) H15···H12iii 3.287 (2)
C26···C3 3.505 (2) H15···H13iii 3.374 (2)
C26···H5 2.958 (2) H15···H14 3.193 (2)
C26···H16 0.979 H15···H14iii 3.375 (2)
C26···H15 1.957 (2) H11···H12 2.317 (3)
C26···H14 3.310 (2) H12···H13 2.476 (3)
C26···H17 2.692 (2) H13···H14 2.284 (2)
C26···H21 3.407 (3) H13···H19ii 3.365 (2)
C6···C7 1.392 (2) H13···H21ii 3.502 (3)
C6···C8 2.442 (2) H13···H22ii 3.269 (3)
C6···C4 2.399 (2) H14···H17 2.895 (2)
C6···C3 2.805 (2) H14···H18ii 3.515 (2)
C6···H3 0.960 H14···H21 2.906 (3)
C6···H4 2.075 (2) H17···H18 2.422 (2)
C6···H1 3.265 (2) H17···H22ii 2.616 (3)
C6···H12iii 3.378 (2) H18···H19 2.315 (2)
C6···H13iii 3.168 (2) H18···H22ii 2.812 (3)
C6···H19x 3.464 (2) H19···H20 2.393 (2)
C6···H20x 3.497 (2) H21···H22 1.667
C19···C20 1.406 (2)
Co1—Co2—C36 148.16 (5) C20—C19—C18 120.62 (15) Co1—Co2—C38 102.69 (5) C6—C7—C8 121.77 (13)
C36—Co2—C38 103.12 (7) C6—C7—H4 120.37 (9)
Co1—Co2—C2 51.49 (4) C8—C7—H4 117.61 (8)
C36—Co2—C2 107.38 (6) C17—C16—C11 119.64 (14) C38—Co2—C2 95.86 (6) C17—C16—C15 120.74 (15) Co1—Co2—C37 93.61 (5) C11—C16—C15 119.61 (15) C36—Co2—C37 96.93 (7) C19—C20—C21 120.68 (17) C38—Co2—C37 105.88 (7) C19—C20—H11 118.39 (11) C2—Co2—C37 142.66 (6) C21—C20—H11 120.8 (1) Co1—Co2—C1 51.75 (4) C16—C17—C18 178.10 (17)
C36—Co2—C1 96.50 (6) C9—C8—C7 122.61 (13)
C38—Co2—C1 135.39 (6) C9—C8—C3 119.41 (13)
C2—Co2—C1 39.70 (6) C7—C8—C3 117.97 (13)
C37—Co2—C1 111.03 (6) C24—C25—C26 132.23 (14) Co2—Co1—C2 51.96 (4) C24—C25—H15 111.39 (8) Co2—Co1—C35 99.43 (5) C26—C25—H15 116.37 (9) C2—Co1—C35 137.84 (6) Co1—C34—O2 177.58 (13) Co2—Co1—C33 149.01 (5) C19—C18—C17 177.53 (17) C2—Co1—C33 97.73 (6) C16—C11—C10 119.76 (14) C35—Co1—C33 101.36 (7) C16—C11—C12 118.83 (14) Co2—Co1—C1 51.65 (4) C10—C11—C12 120.95 (14)
C2—Co1—C1 39.81 (6) C5—C4—C3 121.54 (13)
C35—Co1—C1 99.08 (6) C5—C4—H1 120.37 (8)
C33—Co1—C1 102.20 (6) C3—C4—H1 117.96 (8)
Co2—Co1—C34 95.67 (5) C9—C10—C11 130.91 (14)
C2—Co1—C34 107.09 (6) C9—C10—H6 116.15 (9)
C35—Co1—C34 105.92 (7) C11—C10—H6 112.93 (8) C33—Co1—C34 100.39 (7) C15—C14—C13 120.25 (15) C1—Co1—C34 142.01 (6) C15—C14—H9 119.6 (1) Co2—C36—O4 176.47 (14) C13—C14—H9 120.1 (1) Co2—C38—O6 175.91 (14) C1—C32—C27 123.12 (12) Co2—C2—Co1 76.55 (5) C1—C32—C31 117.95 (13) Co2—C2—C1 69.81 (8) C27—C32—C31 118.91 (13) Co1—C2—C1 70.37 (8) C30—C29—C28 119.70 (14)
Co2—C2—C3 131.4 (1) C30—C29—H18 115.79 (9)
Co1—C2—C3 132.4 (1) C28—C29—H18 124.38 (9)
C1—C2—C3 147.39 (14) C16—C15—C14 120.40 (16) C6—C5—C4 119.39 (13) C16—C15—H10 114.7 (1)
C6—C5—H2 118.29 (8) C14—C15—H10 124.8 (1)
Co1—C35—O3 176.84 (13) C14—C13—H8 118.3 (1) C8—C9—C10 130.99 (14) C12—C13—H8 121.9 (1) C8—C9—H5 114.39 (8) C24—C23—C22 120.96 (16) C10—C9—H5 114.58 (9) C24—C23—H14 119.0 (1) Co1—C33—O1 177.93 (14) C22—C23—H14 119.80 (11) C19—C24—C25 119.38 (14) C20—C21—C22 120.21 (16) C19—C24—C23 118.82 (14) C20—C21—H12 117.3 (1) C25—C24—C23 121.26 (14) C22—C21—H12 122.5 (1) Co2—C37—O5 177.49 (14) C27—C28—C29 121.90 (14) C29—C30—C31 119.66 (13) C27—C28—H17 118.56 (9) C29—C30—H19 121.29 (9) C29—C28—H17 119.28 (9) C31—C30—H19 119.06 (9) C2—C3—C8 121.93 (13)
Co2—C1—Co1 76.60 (5) C2—C3—C4 118.80 (13)
Co2—C1—C2 70.49 (9) C8—C3—C4 119.27 (13)
Co1—C1—C2 69.83 (8) C30—C31—C32 121.74 (14) Co2—C1—C32 132.5 (1) C30—C31—H20 124.37 (9) Co1—C1—C32 132.0 (1) C32—C31—H20 113.88 (8) C2—C1—C32 146.72 (13) C11—C12—C13 121.10 (16) C26—C27—C32 119.26 (13) C11—C12—H7 120.59 (9) C26—C27—C28 122.66 (13) C13—C12—H7 118.2 (1) C32—C27—C28 118.06 (13) C23—C22—C21 119.86 (16) C27—C26—C25 131.23 (14) C23—C22—H13 113.55 (11) C27—C26—H16 115.11 (8) C21—C22—H13 126.6 (1) C25—C26—H16 113.43 (9) Cl2—C39—Cl1 111.79 (11) C5—C6—C7 120.04 (13) Cl2—C39—H21 106.76 (7)
C5—C6—H3 117.94 (8) Cl1—C39—H21 105.03 (7)
C7—C6—H3 121.88 (8) Cl2—C39—H22 106.45 (7)
C24—C19—C20 119.46 (15) Cl1—C39—H22 105.16 (7) C24—C19—C18 119.92 (14) H21—C39—H22 121.674
C2—Co2—C1—C32 151.4 (3) C20—C19—C18—C17 −129.4 (5) C37—Co2—C1—Co1 77.5 (2) C6—C7—C8—C9 179.5 (2) C37—Co2—C1—C2 150.5 (2) C6—C7—C8—C3 0.2 (3) C37—Co2—C1—C32 −58.1 (3) C11—C16—C17—C18 −5.9 (7) Co2—Co1—C2—Co2 0.00 (2) C15—C16—C17—C18 173.0 (7) Co2—Co1—C2—C1 73.0 (1) C17—C16—C11—C10 6.9 (3) Co2—Co1—C2—C3 −134.7 (3) C17—C16—C11—C12 179.3 (2) C35—Co1—C2—Co2 −56.4 (3) C15—C16—C11—C10 −172.0 (2) C35—Co1—C2—C1 16.7 (3) C15—C16—C11—C12 0.3 (3) C35—Co1—C2—C3 169.0 (2) C17—C16—C15—C14 −178.6 (2) C33—Co1—C2—Co2 −172.8 (2) C11—C16—C15—C14 0.3 (3) C33—Co1—C2—C1 −99.8 (2) C19—C20—C21—C22 0.3 (4) C33—Co1—C2—C3 52.5 (3) C16—C17—C18—C19 −13.8 (10) C1—Co1—C2—Co2 −73.0 (1) C9—C8—C3—C2 −0.2 (3) C1—Co1—C2—C1 0.0 (1) C9—C8—C3—C4 179.8 (2) C1—Co1—C2—C3 152.3 (3) C7—C8—C3—C2 179.2 (2) C34—Co1—C2—Co2 83.7 (2) C7—C8—C3—C4 −0.8 (3) C34—Co1—C2—C1 156.8 (2) C16—C11—C10—C9 −103.8 (3) C34—Co1—C2—C3 −50.9 (3) C12—C11—C10—C9 84.0 (3) Co2—Co1—C35—O3 −31.3 (4) C16—C11—C12—C13 −0.4 (3) C2—Co1—C35—O3 10.3 (4) C10—C11—C12—C13 171.9 (2) C33—Co1—C35—O3 125.6 (4) C5—C4—C3—C2 −179.1 (2) C1—Co1—C35—O3 21.1 (4) C5—C4—C3—C8 0.9 (3) C34—Co1—C35—O3 −130.1 (4) C13—C14—C15—C16 −0.8 (3) Co2—Co1—C33—O1 −23.8 (7) C15—C14—C13—C12 0.8 (3) C2—Co1—C33—O1 −12.8 (7) C1—C32—C31—C30 −177.3 (2) C35—Co1—C33—O1 −155.0 (7) C27—C32—C31—C30 1.1 (3) C1—Co1—C33—O1 −53.0 (7) C30—C29—C28—C27 0.3 (3) C34—Co1—C33—O1 96.2 (7) C14—C13—C12—C11 −0.2 (3) Co2—Co1—C1—Co2 0.00 (2) C24—C23—C22—C21 −1.1 (3) Co2—Co1—C1—C2 −73.9 (1) C20—C21—C22—C23 0.8 (4) Co2—Co1—C1—C32 136.0 (3)
