1
Supplementary Information
I. Experimental procedure:
Metathesis reaction of TDDA with syn-tricyclooctadiene:
A suspension of TDDA (100 mg, 0.28 mmol), syn-tricyclooctadiene (300 mg, 2.88 mmol) and
naphthalene (20 mg, 0.15 mmol) in benzene (200 ml) was agitated with a stream of argon and
irradiated with a 15 W low-pressure mercury lamp in a quartz photoreactor. After 24 h of
irradiation the solvent was evaporated and the solid residue was dissolved in dichloromethane
and passed through a short column of silical gel. For separation of the products a
semipreparative HPLC silica gel column and a mixture of heptane/dichloromethane 95/5 was
used. The Moebius C2 compound could only be isolated after removing the cyclohexadiene Cs
isomer (which has a very similar retention time) by adding a solution of tetracyanoethylene
(TCNE) (3 mg, 0.023 mmol) in 2 ml of dichloromethane to the corresponding fraction.
Immediate filtration over a short silica column retained the Diels-Alder adduct of the
cyclohexadiene Cs compound and the excess of TCNE and enabled the separation of the two
remaining fully conjugated products.
Möbius C2:
H
H 13’ 12’ H
H
11’
14’
H
3’ 2’
4’
1’
10a’
9a’
H
10’
10b’
5’
H
6’
H
H
H
H
H
8
5
9b
10b
9’
9b’
8’
7’
H
7 6H
9
H
H
9a
1
2
H
H
11
10
10a
4
H
14
12 13
H
H
H
H
3
H
H NMR (500 MHz, CDCl3/TMS):  = 7.709 (ddd, 3J1-H, 2-H = 7.5 Hz, 4J1-H, 3-H = 1.3, 5J1-H, 4-H
= 0.5, 2H, 1-H); 7.516* (m, 2H, 8-H); 7.209* (m, 2H, 4-H); 7.201* (m, 2H, 5-H); 7.184 (ddd,
3
J2-H, 1-H = 7.5 Hz, 4J2-H, 4-H = 1.3, 2H, 2-H); 7.098 (ddd, 3J3-H, 2-H = 7.5 Hz, 3J3-H, 4-H = 7.5,
4
J3-H, 1-H = 1.3, 2H, 3-H); 7.009 (ddd, 3J7-H, 6-H = 7.4 Hz, 3J7-H, 8-H = 7.4, 4J7-H, 5-H = 2.0, 2H, 7HA); 7.003 (ddd, 3J6-H, 7-H = 7.4 Hz, 3J6-H, 7-H = 7.4, 4J6-H, 8-H, = 2.0, 2H, 6-HB); 6.486 (dd,
3
J11-H, 12-H = 12.5 Hz, 4J11-H, 13-H = 1.5, 2H, 11-H); 6.118 (dd, 3J12-H, 11-H = 12.5 Hz, 3J12-H, 13-H =
11.9, 2H, 12-H); 5.940 (dd, 3J14-H, 13-H = 4.7 Hz, 4J14-H, 14’-H = 1.9, 2H, 14-H); 5.690 (dddd,
3
J13-H, 12-H = 11.9 Hz, 3J13-H, 14-H = 4.7, 4J13-H, 14’-H = 1.9, nJ = 0.9, 2H, 13-H). *chemical shifts
were calculated from HSQC spectra.
13
C NMR (125.8 MHz, CDCl3/TMS):  = 140.67 (10-C), 139.92 (9-C), 139.36 (10b-C),
138.93 (9a-C), 138.34 (9b-C), 135.91 (10a-C), 128.09 (1-C), 127.79 (12-C), 127.04 (14-C),
126.42 (6-C), 126.27 (8-C), 126.15 (4-C), 125.97 (3-C), 125.41 (2-C), 125.24 (7-C), 124.89
(11-C), 122.05 (5-C).
UV/Vis (CH2Cl2): max () = 253 (26231), 312 (17251), 400 (broad, 2946) nm.
MS (70 eV): m/z (%): 456 (100) [M+].
1
2
Hückel Cs:
H
H 13’ 12’ H
11’
14’
H
H
H
6’ 7’
H
H
5’
8’ H
10b’
H
9b’
10’
10a’
4’
H
5
9b
10b
9
H
H
2’
H
3’
H
8
9’
9a’
1’
7 6H
H
10a
4
H
H
11 12 13
10
9a
1
dihedral
103°
H
H
14
H
3
H
2
H
H NMR (500 MHz, CDCl3/TMS):  = 7.733 (ddd, 3J8-H, 7-H = 7.5 Hz, 4J8-H, 6-H = 1.3, 5J8-H, 5-H
= 0.6, 2H, 8-H); 7.609 (ddd, 3J1-H, 2-H = 7.3 Hz, 4J1-H, 3-H = 1.5, 5J1-H, 4-H = 0.6, 2H, 1-H); 7.332
(ddd, 3J5-H, 6-H = 7.3 Hz, 4J5-H, 7-H = 1.5 Hz, 2H, 5-H); 7.114 (m, 2H, 4-H); 7.087 (ddd,
3
J7-H, 8-H = 7.5 Hz, 3J7-H, 6-H = 7.3, 4J7-H, 5H = 1.5, 2H, 7-H); 7.043 (ddd, 3J6-H, 7-H = 7.3 Hz, 3J6-H,
4
3
3
4
5-H = 7.5, J6-H, 8-H = 1.3, 2H, 6-H); 7.005 (ddd, J2-H, 1-H = 7.3 Hz, J2-H, 3-H = 7.3, J2-H, 4-H =
1.5, 2H, 2-H); 6.978 (ddd, 3J3-H, 2-H = 7.3 Hz, 3J3-H, 4-H = 7.5, 4J3-H, 1-H, = 1.5, 2H, 3-H); 6.624
(dd, 3J12-H, 11-H = 11.0 Hz, 3J12-H, 13-H = 10.8, 2H, 12-H); 6.260 (dd, 3J11-H, 12-H = 11.0 Hz,
4
J11-H, 13-H = 1.3, 2H, 11-H); 6.238 (ddd, 3J14-H, 14’-H = 11.0 Hz, 3J14-H, 13-H = 2.4, 4J14-H, 13’-H =
1.1, 2H, 14-H); 5.875 (dddd, 3J13-H, 12-H = 10.8 Hz, 3J13-H, 14-H = 2.4, 4J13-H, 14’-H = 1.1, 4J13-H, 11-H
= 0.9, 2H, 13-H).
13
C NMR (125.8 MHz, CDCl3/TMS):  = 139.76 (9-C)*, 138.19 (10-C)*, 137.93 (10a-C)*,
137.65 (9b-C)*, 137.47 (9a-C)*, 136.31 (10b-C)*, 131.52 (13-C), 129.83 (14-C), 128.45 (8C), 128.02 (12-C), 127.94 (1-C), 126.44 (3-C), 126.06 (6-C), 125.41 (5-C), 125.23 (7-C),
124.60 (2-C), 123.29 (4-C), 122.00 (11). *assignement according to a CSGT B3LYP/6-31G*
calculation.
UV/Vis (CH2Cl2): max () = 259 (17027), 299 (16334) nm.
MS (70 eV): m/z (%): 456 (100) [M+].
1
UV spectra:
30 000


max = 253 nm
 = 26 231
Möbius C2
20 000
Hückel Cs


max = 259 nm
 = 17 027
max = 312 nm
 = 17 251

max = 299 nm
 = 16 334
10 000

max = 400 nm
 = 2 946
250
300
350
400
450
500
550
 [nm]
3
X-ray data:
Möbius C2:
4
data_oeda_n6a
5
# SUBMISSION DETAILS
data_oeda_n6a
_publ_contact_author
;
Herges, Rainer
**** type your address here and complete the following *****
;
Institut fuer Organische Chemie
Universitaet Kiel
Otto-Hahn-Platz 4
24118 Kiel
Germany
_publ_contact_author_phone
+49 431 880 2440
_publ_contact_author_fax
+49 431 880 1558
_publ_contact_author_email
rherges@oc.uni-kiel.de
_publ_requested_journal
Nature
_publ_requested_coeditor_name
Dariush Ajami
_publ_contact_letter
; Please consider this CIF submission for publication in
***** please complete ******
;
#==========================================================================
====
# TITLE AND AUTHOR LIST
_publ_section_title
; **** Synthesis of a Moebius aromatic hydrocarbon ****
;
loop_
_publ_author_name
_publ_author_address
;
'Ajami, Dariush'
Institut fuer Organische Chemie
Universitaet Kiel
Otto-Hahn-Platz 4
24118 Kiel
Germany
;
;
'Oeckler, Oliver'
Max-Planck-Institut f\"ur Festk\"orperforschung
Heisenbergstra\&se 1
70569 Stuttgart
Bundesrepublik Deutschland
;
;
'Simon, Arndt'
Max-Planck-Institut f\"ur Festk\"orperforschung
Heisenbergstra\&se 1
70569 Stuttgart
Bundesrepublik Deutschland
;
;
;
'Herges, Rainer'
Institut fuer Organische Chemie
Universitaet Kiel
Otto-Hahn-Platz 4
24118 Kiel
Germany
6
***** complete author list !!!
***********
#==========================================================================
====
_audit_creation_method
_chemical_name_systematic
;
?
;
_chemical_name_common
_chemical_melting_point
_chemical_formula_moiety
_chemical_formula_sum
'C36 H24'
_chemical_formula_weight
SHELXL-97
TDDA-TCOD-Moebius-C2-atEcZcEt
?
?
456.55
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C'
0.0033
0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H'
0.0000
0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting
_symmetry_space_group_name_H-M
monoclinic
'C2/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a
_cell_length_b
_cell_length_c
_cell_angle_alpha
_cell_angle_beta
_cell_angle_gamma
_cell_volume
_cell_formula_units_Z
_cell_measurement_temperature
_cell_measurement_reflns_used
_cell_measurement_theta_min
_cell_measurement_theta_max
16.280(2)
10.9590(10)
14.373(2)
90.00
110.41(2)
90.00
2403.3(5)
4
173(2)
9482
2.2
32
_exptl_crystal_description
_exptl_crystal_colour
_exptl_crystal_size_max
_exptl_crystal_size_mid
_exptl_crystal_size_min
_exptl_crystal_density_meas
_exptl_crystal_density_diffrn
'irregular polyhedron'
'yellow'
0.55
0.35
0.10
?
1.262
7
_exptl_crystal_density_method
_exptl_crystal_F_000
_exptl_absorpt_coefficient_mu
_exptl_absorpt_correction_type
_exptl_absorpt_correction_T_min
_exptl_absorpt_correction_T_max
_exptl_absorpt_process_details
'not measured'
960
0.071
multi-scan
0.74
0.93
?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature
173(2)
_diffrn_measurement_device
'2-circle goniometer'
_diffrn_measurement_device_type
'STOE IPDS 2'
_diffrn_detector
'image plate (34 cm diameter)'
_diffrn_detector_type
'STOE'
_diffrn_detector_area_resol_mean
6.67
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage
50
_diffrn_source_current
55
_diffrn_source_power
2.75
_diffrn_radiation_type
'Mo K\a'
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_monochromator
'plane graphite'
_diffrn_radiation_polarisn_norm
0
_diffrn_radiation_collimation
'0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method
'rotation method'
_diffrn_measurement_details
; 180 frames, 1 deg per frame
;
_diffrn_standards_number
_diffrn_standards_interval_count
_diffrn_standards_interval_time
_diffrn_standards_decay_%
_diffrn_reflns_number
_diffrn_reflns_av_R_equivalents
_diffrn_reflns_av_sigmaI/netI
_diffrn_reflns_limit_h_min
_diffrn_reflns_limit_h_max
_diffrn_reflns_limit_k_min
_diffrn_reflns_limit_k_max
_diffrn_reflns_limit_l_min
_diffrn_reflns_limit_l_max
_diffrn_reflns_theta_min
_diffrn_reflns_theta_max
_reflns_number_total
_reflns_number_gt
_reflns_threshold_expression
_computing_data_collection
_computing_cell_refinement
_computing_data_reduction
_computing_structure_solution
_computing_structure_refinement
_computing_molecular_graphics
_computing_publication_material
0
0
0
0
28913
0.0813
0.0289
-21
21
-14
14
-18
18
2.29
27.50
2766
2356
>2sigma(I)
'STOE X-AREA'
'STOE X-AREA'
'STOE X-RED'
'SHELXS-97 (Sheldrick, 1990)'
'SHELXL-97 (Sheldrick, 1997)'
?
?
_refine_special_details
;
Refinement of F^2^ against ALL reflections.
The weighted R-factor wR and
8
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and Rfactors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type
full
_refine_ls_weighting_scheme
calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.5792P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary
direct
_atom_sites_solution_secondary
difmap
_atom_sites_solution_hydrogens
difmap
_refine_ls_hydrogen_treatment
refall
_refine_ls_extinction_method
SHELXL
_refine_ls_extinction_coef
0.0159(15)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns
2766
_refine_ls_number_parameters
212
_refine_ls_number_restraints
0
_refine_ls_R_factor_all
0.0465
_refine_ls_R_factor_gt
0.0400
_refine_ls_wR_factor_ref
0.1132
_refine_ls_wR_factor_gt
0.1097
_refine_ls_goodness_of_fit_ref
1.046
_refine_ls_restrained_S_all
1.046
_refine_ls_shift/su_max
0.000
_refine_ls_shift/su_mean
0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48559(10) -0.30404(12) 0.20056(12) 0.0580(4) Uani 1 1 d . . .
C2 C 0.46442(9) -0.21045(12) 0.12430(11) 0.0499(3) Uani 1 1 d . . .
C3 C 0.42689(8) -0.09937(11) 0.11694(9) 0.0423(3) Uani 1 1 d . . .
C4 C 0.39481(7) -0.03693(10) 0.18639(8) 0.0350(3) Uani 1 1 d . . .
C5 C 0.37108(7) 0.08223(9) 0.17682(8) 0.0317(2) Uani 1 1 d . . .
C6 C 0.37090(7) 0.16135(9) 0.09285(8) 0.0313(2) Uani 1 1 d . . .
C7 C 0.32757(7) 0.13280(10) -0.00709(8) 0.0352(3) Uani 1 1 d . . .
C8 C 0.32570(8) 0.21534(11) -0.08069(8) 0.0388(3) Uani 1 1 d . . .
C9 C 0.36605(8) 0.32770(11) -0.05554(9) 0.0407(3) Uani 1 1 d . . .
C10 C 0.41004(8) 0.35788(11) 0.04338(8) 0.0374(3) Uani 1 1 d . . .
C11 C 0.41341(7) 0.27510(9) 0.11815(8) 0.0316(2) Uani 1 1 d . . .
C12 C 0.45600(7) 0.29525(9) 0.22685(8) 0.0312(2) Uani 1 1 d . . .
C13 C 0.39376(7) 0.26784(10) 0.27931(8) 0.0327(2) Uani 1 1 d . . .
C14 C 0.37394(8) 0.34363(12) 0.34601(9) 0.0414(3) Uani 1 1 d . . .
C15 C 0.31301(9) 0.30669(14) 0.38836(9) 0.0493(3) Uani 1 1 d . . .
C16 C 0.27384(9) 0.19328(14) 0.36632(9) 0.0483(3) Uani 1 1 d . . .
9
C17 C 0.29382(8) 0.11562(12) 0.30075(9) 0.0399(3) Uani 1 1 d . . .
C18 C 0.35234(7) 0.15308(10) 0.25525(8) 0.0328(2) Uani 1 1 d . . .
H1 H 0.4809(13) -0.3912(18) 0.1713(14) 0.079(6) Uiso 1 1 d . . .
H2 H 0.4793(11) -0.2349(15) 0.0616(13) 0.061(5) Uiso 1 1 d . . .
H3 H 0.4215(10) -0.0520(14) 0.0528(11) 0.046(4) Uiso 1 1 d . . .
H4 H 0.3980(9) -0.0820(12) 0.2533(10) 0.034(3) Uiso 1 1 d . . .
H7 H 0.2952(9) 0.0556(14) -0.0248(10) 0.041(3) Uiso 1 1 d . . .
H8 H 0.2955(9) 0.1937(13) -0.1520(11) 0.043(4) Uiso 1 1 d . . .
H9 H 0.3635(11) 0.3871(14) -0.1083(12) 0.052(4) Uiso 1 1 d . . .
H10 H 0.4385(10) 0.4375(15) 0.0609(11) 0.046(4) Uiso 1 1 d . . .
H14 H 0.4020(10) 0.4222(14) 0.3622(11) 0.046(4) Uiso 1 1 d . . .
H15 H 0.2981(11) 0.3625(15) 0.4330(12) 0.056(4) Uiso 1 1 d . . .
H16 H 0.2285(12) 0.1679(16) 0.3957(13) 0.061(4) Uiso 1 1 d . . .
H17 H 0.2657(10) 0.0352(15) 0.2845(11) 0.047(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0495(8) 0.0286(6) 0.0810(10) -0.0107(6) 0.0041(7) 0.0027(5)
C2 0.0421(7) 0.0447(7) 0.0530(8) -0.0153(6) 0.0042(6) 0.0040(5)
C3 0.0382(6) 0.0404(6) 0.0412(6) -0.0062(5) 0.0051(5) 0.0025(5)
C4 0.0318(5) 0.0297(5) 0.0385(6) 0.0007(4) 0.0059(4) -0.0003(4)
C5 0.0280(5) 0.0304(5) 0.0321(5) 0.0011(4) 0.0048(4) 0.0004(4)
C6 0.0299(5) 0.0298(5) 0.0310(5) -0.0005(4) 0.0064(4) 0.0027(4)
C7 0.0331(5) 0.0335(5) 0.0341(6) -0.0041(4) 0.0056(4) 0.0008(4)
C8 0.0378(6) 0.0439(6) 0.0292(5) -0.0022(4) 0.0046(4) 0.0033(5)
C9 0.0434(6) 0.0424(6) 0.0319(6) 0.0070(5) 0.0077(5) 0.0015(5)
C10 0.0394(6) 0.0334(5) 0.0342(6) 0.0034(4) 0.0061(5) -0.0010(4)
C11 0.0315(5) 0.0295(5) 0.0292(5) 0.0000(4) 0.0049(4) 0.0021(4)
C12 0.0367(5) 0.0231(4) 0.0290(5) 0.0005(4) 0.0055(4) 0.0023(4)
C13 0.0326(5) 0.0330(5) 0.0271(5) 0.0030(4) 0.0036(4) 0.0088(4)
C14 0.0428(6) 0.0420(6) 0.0336(6) -0.0017(5) 0.0063(5) 0.0129(5)
C15 0.0503(7) 0.0626(8) 0.0337(6) 0.0002(5) 0.0130(5) 0.0207(6)
C16 0.0439(7) 0.0651(8) 0.0371(6) 0.0129(6) 0.0156(5) 0.0137(6)
C17 0.0371(6) 0.0458(6) 0.0343(6) 0.0123(5) 0.0092(5) 0.0070(5)
C18 0.0307(5) 0.0339(5) 0.0293(5) 0.0063(4) 0.0050(4) 0.0074(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.332(3) 2_655 ?
C1 C2 1.452(2) . ?
C1 H1 1.04(2) . ?
C2 C3 1.3496(18) . ?
10
C2 H2 1.047(17) . ?
C3 C4 1.4494(17) . ?
C3 H3 1.034(15) . ?
C4 C5 1.3552(15) . ?
C4 H4 1.067(13) . ?
C5 C6 1.4853(14) . ?
C5 C18 1.4854(15) . ?
C6 C7 1.3971(15) . ?
C6 C11 1.4106(14) . ?
C7 C8 1.3841(17) . ?
C7 H7 0.983(15) . ?
C8 C9 1.3831(17) . ?
C8 H8 0.998(15) . ?
C9 C10 1.3906(16) . ?
C9 H9 0.989(15) . ?
C10 C11 1.3927(15) . ?
C10 H10 0.979(16) . ?
C11 C12 1.4883(14) . ?
C12 C12 1.353(2) 2_655 ?
C12 C13 1.4894(15) . ?
C13 C14 1.3887(15) . ?
C13 C18 1.4119(16) . ?
C14 C15 1.393(2) . ?
C14 H14 0.964(16) . ?
C15 C16 1.382(2) . ?
C15 H15 0.977(16) . ?
C16 C17 1.3899(19) . ?
C16 H16 1.009(17) . ?
C17 C18 1.3923(16) . ?
C17 H17 0.983(16) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C2 135.06(8) 2_655 . ?
C1 C1 H1 112.5(10) 2_655 . ?
C2 C1 H1 112.3(10) . . ?
C3 C2 C1 132.69(14) . . ?
C3 C2 H2 113.4(9) . . ?
C1 C2 H2 113.9(9) . . ?
C2 C3 C4 129.33(13) . . ?
C2 C3 H3 114.7(8) . . ?
C4 C3 H3 116.0(8) . . ?
C5 C4 C3 122.92(11) . . ?
C5 C4 H4 117.4(7) . . ?
C3 C4 H4 119.1(7) . . ?
C4 C5 C6 124.38(10) . . ?
C4 C5 C18 123.60(10) . . ?
C6 C5 C18 111.64(8) . . ?
C7 C6 C11 119.30(10) . . ?
C7 C6 C5 124.19(10) . . ?
C11 C6 C5 116.40(9) . . ?
C8 C7 C6 120.54(10) . . ?
C8 C7 H7 119.9(8) . . ?
C6 C7 H7 119.5(8) . . ?
C9 C8 C7 120.01(10) . . ?
C9 C8 H8 119.9(8) . . ?
C7 C8 H8 120.1(8) . . ?
11
C8 C9 C10 120.48(11) . . ?
C8 C9 H9 119.8(9) . . ?
C10 C9 H9 119.7(9) . . ?
C9 C10 C11 120.12(11) . . ?
C9 C10 H10 120.2(8) . . ?
C11 C10 H10 119.7(8) . . ?
C10 C11 C6 119.53(10) . . ?
C10 C11 C12 126.30(10) . . ?
C6 C11 C12 114.13(9) . . ?
C12 C12 C11 122.82(12) 2_655 . ?
C12 C12 C13 122.80(12) 2_655 . ?
C11 C12 C13 110.57(9) . . ?
C14 C13 C18 119.72(11) . . ?
C14 C13 C12 126.28(11) . . ?
C18 C13 C12 114.00(9) . . ?
C13 C14 C15 120.01(12) . . ?
C13 C14 H14 119.8(9) . . ?
C15 C14 H14 120.2(9) . . ?
C16 C15 C14 120.21(12) . . ?
C16 C15 H15 120.9(10) . . ?
C14 C15 H15 118.9(10) . . ?
C15 C16 C17 120.50(12) . . ?
C15 C16 H16 119.9(10) . . ?
C17 C16 H16 119.5(10) . . ?
C16 C17 C18 119.88(12) . . ?
C16 C17 H17 120.7(9) . . ?
C18 C17 H17 119.4(9) . . ?
C17 C18 C13 119.62(10) . . ?
C17 C18 C5 123.89(10) . . ?
C13 C18 C5 116.40(9) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 -37.0(4) 2_655 . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 169.29(13) . . . . ?
C3 C4 C5 C6 2.95(17) . . . . ?
C3 C4 C5 C18 -169.43(10) . . . . ?
C4 C5 C6 C7 53.63(16) . . . . ?
C18 C5 C6 C7 -133.20(11) . . . . ?
C4 C5 C6 C11 -130.23(11) . . . . ?
C18 C5 C6 C11 42.94(12) . . . . ?
C11 C6 C7 C8 -0.45(16) . . . . ?
C5 C6 C7 C8 175.59(10) . . . . ?
C6 C7 C8 C9 -0.75(17) . . . . ?
C7 C8 C9 C10 1.15(18) . . . . ?
C8 C9 C10 C11 -0.33(18) . . . . ?
C9 C10 C11 C6 -0.87(17) . . . . ?
C9 C10 C11 C12 -178.52(11) . . . . ?
C7 C6 C11 C10 1.25(15) . . . . ?
C5 C6 C11 C10 -175.09(10) . . . . ?
C7 C6 C11 C12 179.17(9) . . . . ?
C5 C6 C11 C12 2.84(13) . . . . ?
C10 C11 C12 C12 -73.58(12) . . . 2_655 ?
12
C6 C11 C12 C12 108.66(9) . . . 2_655 ?
C10 C11 C12 C13 127.88(11) . . . . ?
C6 C11 C12 C13 -49.88(12) . . . . ?
C12 C12 C13 C14 72.93(12) 2_655 . . . ?
C11 C12 C13 C14 -128.53(11) . . . . ?
C12 C12 C13 C18 -107.70(9) 2_655 . . . ?
C11 C12 C13 C18 50.84(11) . . . . ?
C18 C13 C14 C15 -0.43(16) . . . . ?
C12 C13 C14 C15 178.91(11) . . . . ?
C13 C14 C15 C16 1.76(18) . . . . ?
C14 C15 C16 C17 -0.89(19) . . . . ?
C15 C16 C17 C18 -1.33(18) . . . . ?
C16 C17 C18 C13 2.64(16) . . . . ?
C16 C17 C18 C5 -173.63(10) . . . . ?
C14 C13 C18 C17 -1.77(15) . . . . ?
C12 C13 C18 C17 178.82(9) . . . . ?
C14 C13 C18 C5 174.78(9) . . . . ?
C12 C13 C18 C5 -4.63(13) . . . . ?
C4 C5 C18 C17 -52.30(15) . . . . ?
C6 C5 C18 C17 134.46(11) . . . . ?
C4 C5 C18 C13 131.32(11) . . . . ?
C6 C5 C18 C13 -41.92(12) . . . . ?
_diffrn_measured_fraction_theta_max
_diffrn_reflns_theta_full
_diffrn_measured_fraction_theta_full
_refine_diff_density_max
0.249
_refine_diff_density_min
-0.216
_refine_diff_density_rms
0.054
0.999
27.50
0.999