# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global_9-(9-Phenanthryl)tetracyclo[3.3.2.0(6,8).0(4,10)]dec-2-en
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Dieter E. Kaufmann'
_publ_contact_author_address     
# Name and address of author for correspondence
;
Professor Dr. Dieter E. Kaufmann
Institut fuer Organische Chemie
der Technischen Universitaet Clausthal
Leibnizstr. 6
38678 Clausthal-Zellerfeld
Germany
;
_publ_contact_author_phone       '+49(0)5323 72-2027, -2026'
_publ_contact_author_fax         '+49(0)5323 72-2834'
_publ_contact_author_email       dieter.kaufmann@tu-clausthal.de

_publ_section_title              
;
Palladium-catalyzed, stereoselective rearrangement of a tetracyclic
allyl cyclopropane under arylation
;
loop_
_publ_author_name
'Joerg Storsberg'
'Min-Liang Yao'
'Nueket Oecal'
'A.de Meijere'
'Arnold E.W. Adam'
;
D.E.Kaufmann
;

#============================================================================

data_9-(9-Phenanthryl)tetracyclo[3.3.2.0(6,8).0(4,10)]dec-2-en
_database_code_depnum_ccdc_archive 'CCDC 221115'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'9-(9-Phenanthryl)tetracyclo[3.3.2.0(6,8).0(4,10)]dec-2-en'
;
_chemical_name_common            
9-(9-Phenanthryl)tetracyclo(3.3.2.0(6,8).0(4,10))dec-2-en
_chemical_melting_point          154
_chemical_formula_moiety         'C24 H20'
_chemical_formula_sum            'C48 H40'
_chemical_formula_weight         616.80

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           monoclinic
_symmetry_space_group_name_H-M   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                   22.183(7)
_cell_length_b                   6.6592(12)
_cell_length_c                   22.362(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.17(2)
_cell_angle_gamma                90.00
_cell_volume                     3300.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'irregular polyhedron'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
see publication
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'IPDS I, Stoe, Darmstadt, Germany'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10340
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         23.99
_reflns_number_total             2500
_reflns_number_gt                1352
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows, POV-Ray 3.1'
_computing_publication_material  'MS Office'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
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 R-
factors 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
[0.00000+1.00000exp(3.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0271P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2500
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 0.38666(8) -0.0290(3) 0.04900(9) 0.0460(5) Uani 1 1 d . . .
C2 C 0.45195(9) 0.0114(3) 0.06234(10) 0.0516(5) Uani 1 1 d . . .
C3 C 0.48407(10) -0.1175(3) 0.09404(10) 0.0581(6) Uani 1 1 d . . .
C4 C 0.45749(9) -0.2938(3) 0.12145(11) 0.0603(6) Uani 1 1 d . . .
C5 C 0.41471(11) -0.4285(3) 0.08404(12) 0.0669(7) Uani 1 1 d . . .
C6 C 0.40315(11) -0.3941(3) 0.01876(12) 0.0663(6) Uani 1 1 d . . .
C7 C 0.34013(12) -0.3562(4) -0.00398(15) 0.0772(7) Uani 1 1 d . . .
C8 C 0.38418(9) -0.1885(3) -0.00005(11) 0.0569(6) Uani 1 1 d . . .
C9 C 0.35724(8) -0.1052(3) 0.10670(9) 0.0438(5) Uani 1 1 d . . .
C10 C 0.39055(9) -0.2877(3) 0.12895(11) 0.0550(6) Uani 1 1 d . . .
C11 C 0.35267(7) 0.0554(2) 0.15442(8) 0.0405(5) Uani 1 1 d . . .
C12 C 0.30641(7) 0.2079(3) 0.14892(8) 0.0410(5) Uani 1 1 d . . .
C13 C 0.26527(8) 0.2135(3) 0.09939(10) 0.0509(5) Uani 1 1 d . . .
C14 C 0.22188(9) 0.3571(3) 0.09437(11) 0.0607(6) Uani 1 1 d . . .
C15 C 0.21694(9) 0.4995(4) 0.13909(11) 0.0635(6) Uani 1 1 d . . .
C16 C 0.25577(9) 0.4979(3) 0.18786(10) 0.0547(5) Uani 1 1 d . . .
C17 C 0.30172(7) 0.3556(3) 0.19433(9) 0.0427(5) Uani 1 1 d . . .
C18 C 0.34421(7) 0.3579(3) 0.24565(8) 0.0421(5) Uani 1 1 d . . .
C19 C 0.34414(9) 0.5024(3) 0.29159(10) 0.0538(5) Uani 1 1 d . . .
C20 C 0.38546(10) 0.4982(4) 0.33882(10) 0.0606(6) Uani 1 1 d . . .
C21 C 0.42859(10) 0.3496(3) 0.34227(11) 0.0585(6) Uani 1 1 d . . .
C22 C 0.43027(8) 0.2078(3) 0.29837(9) 0.0535(5) Uani 1 1 d . . .
C23 C 0.38860(7) 0.2083(3) 0.24918(9) 0.0437(5) Uani 1 1 d . . .
C24 C 0.39078(8) 0.0600(3) 0.20310(9) 0.0461(5) Uani 1 1 d . . .
H1 H 0.3661(8) 0.098(3) 0.0336(8) 0.051(5) Uiso 1 1 d . . .
H2 H 0.4685(9) 0.136(3) 0.0444(9) 0.070(6) Uiso 1 1 d . . .
H3 H 0.5258(10) -0.101(3) 0.1023(9) 0.071(6) Uiso 1 1 d . . .
H4 H 0.4808(9) -0.363(3) 0.1535(10) 0.066(6) Uiso 1 1 d . . .
H5 H 0.4155(8) -0.561(3) 0.0968(9) 0.056(5) Uiso 1 1 d . . .
H6 H 0.4286(10) -0.466(3) -0.0078(11) 0.085(8) Uiso 1 1 d . . .
H71 H 0.3286(10) -0.402(4) -0.0437(12) 0.088(8) Uiso 1 1 d . . .
H72 H 0.3103(10) -0.373(3) 0.0286(12) 0.086(8) Uiso 1 1 d . . .
H8 H 0.3990(9) -0.141(3) -0.0389(10) 0.067(6) Uiso 1 1 d . . .
H9 H 0.3164(8) -0.146(2) 0.0942(7) 0.038(4) Uiso 1 1 d . . .
H10 H 0.3780(8) -0.341(3) 0.1654(9) 0.049(5) Uiso 1 1 d . . .
H13 H 0.2668(7) 0.116(3) 0.0684(9) 0.044(5) Uiso 1 1 d . . .
H14 H 0.1949(9) 0.355(3) 0.0606(10) 0.066(6) Uiso 1 1 d . . .
H15 H 0.1867(9) 0.604(3) 0.1342(9) 0.070(6) Uiso 1 1 d . . .
H16 H 0.2527(8) 0.602(3) 0.2177(9) 0.059(6) Uiso 1 1 d . . .
H19 H 0.3153(8) 0.609(3) 0.2887(8) 0.049(5) Uiso 1 1 d . . .
H20 H 0.3854(8) 0.607(3) 0.3711(10) 0.066(6) Uiso 1 1 d . . .
H21 H 0.4563(9) 0.349(3) 0.3760(10) 0.063(6) Uiso 1 1 d . . .
H22 H 0.4607(8) 0.096(3) 0.3007(9) 0.063(6) Uiso 1 1 d . . .
H24 H 0.4207(8) -0.044(3) 0.2093(8) 0.052(5) 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 0.0491(11) 0.0445(12) 0.0447(14) -0.0014(9) 0.0058(9) 0.0021(9)
C2 0.0546(12) 0.0469(12) 0.0546(15) -0.0072(10) 0.0171(10) -0.0047(10)
C3 0.0444(12) 0.0630(14) 0.0676(17) -0.0147(12) 0.0086(10) 0.0000(11)
C4 0.0600(13) 0.0536(13) 0.0672(17) -0.0017(11) 0.0010(11) 0.0165(10)
C5 0.0863(16) 0.0337(11) 0.081(2) -0.0017(11) 0.0082(13) 0.0059(11)
C6 0.0725(15) 0.0560(14) 0.071(2) -0.0186(12) 0.0063(12) 0.0016(11)
C7 0.0775(17) 0.0789(17) 0.075(2) -0.0290(14) 0.0002(15) -0.0126(13)
C8 0.0605(12) 0.0579(14) 0.0526(16) -0.0092(11) 0.0067(10) -0.0006(10)
C9 0.0398(10) 0.0450(11) 0.0469(14) -0.0030(8) 0.0044(8) -0.0043(8)
C10 0.0682(13) 0.0391(11) 0.0585(16) 0.0067(10) 0.0134(11) -0.0016(9)
C11 0.0351(10) 0.0459(11) 0.0409(13) 0.0035(8) 0.0072(8) -0.0009(8)
C12 0.0341(9) 0.0470(10) 0.0423(14) 0.0042(9) 0.0063(8) -0.0029(8)
C13 0.0440(11) 0.0629(13) 0.0457(15) -0.0031(10) 0.0019(9) 0.0050(10)
C14 0.0464(12) 0.0825(17) 0.0528(17) 0.0053(12) -0.0041(10) 0.0120(11)
C15 0.0506(12) 0.0721(15) 0.0678(19) 0.0037(12) 0.0011(11) 0.0213(11)
C16 0.0505(12) 0.0567(13) 0.0572(16) -0.0034(11) 0.0048(11) 0.0110(10)
C17 0.0385(10) 0.0454(11) 0.0447(13) 0.0054(9) 0.0101(8) 0.0003(8)
C18 0.0399(10) 0.0452(11) 0.0418(13) 0.0026(8) 0.0084(8) -0.0049(8)
C19 0.0528(12) 0.0531(12) 0.0559(16) -0.0046(10) 0.0073(11) 0.0000(10)
C20 0.0642(14) 0.0663(14) 0.0516(17) -0.0096(11) 0.0031(11) -0.0119(12)
C21 0.0514(12) 0.0770(16) 0.0467(16) 0.0000(12) -0.0036(10) -0.0146(11)
C22 0.0417(11) 0.0691(14) 0.0494(16) 0.0055(11) -0.0012(10) -0.0008(10)
C23 0.0366(10) 0.0524(11) 0.0425(13) 0.0040(9) 0.0069(8) -0.0026(8)
C24 0.0397(10) 0.0514(12) 0.0475(14) 0.0041(9) 0.0065(9) 0.0078(9)

_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 C2 1.492(3) . ?
C1 C8 1.526(3) . ?
C1 C9 1.553(3) . ?
C1 H1 1.014(18) . ?
C2 C3 1.307(3) . ?
C2 H2 1.00(2) . ?
C3 C4 1.459(3) . ?
C3 H3 0.94(2) . ?
C4 C10 1.501(3) . ?
C4 C5 1.531(3) . ?
C4 H4 0.98(2) . ?
C5 C10 1.489(3) . ?
C5 C6 1.490(3) . ?
C5 H5 0.926(19) . ?
C6 C8 1.488(3) . ?
C6 C7 1.491(3) . ?
C6 H6 0.96(2) . ?
C7 C8 1.485(3) . ?
C7 H71 0.96(3) . ?
C7 H72 1.01(2) . ?
C8 H8 0.99(2) . ?
C9 C10 1.498(3) . ?
C9 C11 1.517(3) . ?
C9 H9 0.976(16) . ?
C10 H10 0.941(19) . ?
C11 C24 1.353(3) . ?
C11 C12 1.446(2) . ?
C12 C13 1.409(3) . ?
C12 C17 1.420(3) . ?
C13 C14 1.358(3) . ?
C13 H13 0.950(18) . ?
C14 C15 1.386(3) . ?
C14 H14 0.95(2) . ?
C15 C16 1.364(3) . ?
C15 H15 0.97(2) . ?
C16 C17 1.395(3) . ?
C16 H16 0.97(2) . ?
C17 C18 1.457(3) . ?
C18 C23 1.401(2) . ?
C18 C19 1.408(3) . ?
C19 C20 1.372(3) . ?
C19 H19 0.957(18) . ?
C20 C21 1.377(3) . ?
C20 H20 1.02(2) . ?
C21 C22 1.363(3) . ?
C21 H21 0.95(2) . ?
C22 C23 1.410(3) . ?
C22 H22 1.005(19) . ?
C23 C24 1.429(3) . ?
C24 H24 0.964(18) . ?

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
C2 C1 C8 106.11(15) . . ?
C2 C1 C9 109.15(16) . . ?
C8 C1 C9 111.39(16) . . ?
C2 C1 H1 109.8(10) . . ?
C8 C1 H1 109.4(10) . . ?
C9 C1 H1 110.9(10) . . ?
C3 C2 C1 119.67(19) . . ?
C3 C2 H2 124.3(11) . . ?
C1 C2 H2 116.0(11) . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 H3 122.8(13) . . ?
C4 C3 H3 114.7(13) . . ?
C3 C4 C10 116.27(18) . . ?
C3 C4 C5 119.6(2) . . ?
C10 C4 C5 58.80(14) . . ?
C3 C4 H4 118.1(11) . . ?
C10 C4 H4 115.4(12) . . ?
C5 C4 H4 115.1(12) . . ?
C10 C5 C6 120.7(2) . . ?
C10 C5 C4 59.59(14) . . ?
C6 C5 C4 121.7(2) . . ?
C10 C5 H5 113.2(12) . . ?
C6 C5 H5 116.6(12) . . ?
C4 C5 H5 112.7(12) . . ?
C8 C6 C5 117.0(2) . . ?
C8 C6 C7 59.78(16) . . ?
C5 C6 C7 119.0(2) . . ?
C8 C6 H6 116.8(15) . . ?
C5 C6 H6 116.3(15) . . ?
C7 C6 H6 116.0(14) . . ?
C8 C7 C6 60.03(16) . . ?
C8 C7 H71 116.3(15) . . ?
C6 C7 H71 118.2(14) . . ?
C8 C7 H72 119.1(13) . . ?
C6 C7 H72 111.6(14) . . ?
H71 C7 H72 118(2) . . ?
C7 C8 C6 60.19(16) . . ?
C7 C8 C1 124.9(2) . . ?
C6 C8 C1 115.8(2) . . ?
C7 C8 H8 115.2(12) . . ?
C6 C8 H8 116.1(12) . . ?
C1 C8 H8 113.9(12) . . ?
C10 C9 C11 112.55(17) . . ?
C10 C9 C1 108.88(16) . . ?
C11 C9 C1 113.30(15) . . ?
C10 C9 H9 107.9(9) . . ?
C11 C9 H9 108.3(9) . . ?
C1 C9 H9 105.6(9) . . ?
C5 C10 C9 118.2(2) . . ?
C5 C10 C4 61.62(15) . . ?
C9 C10 C4 117.55(18) . . ?
C5 C10 H10 118.4(11) . . ?
C9 C10 H10 115.7(11) . . ?
C4 C10 H10 114.5(11) . . ?
C24 C11 C12 118.18(17) . . ?
C24 C11 C9 121.72(17) . . ?
C12 C11 C9 120.10(16) . . ?
C13 C12 C17 118.76(17) . . ?
C13 C12 C11 121.46(17) . . ?
C17 C12 C11 119.78(16) . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 117.7(11) . . ?
C12 C13 H13 121.0(11) . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 118.8(13) . . ?
C15 C14 H14 121.3(12) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 120.6(12) . . ?
C14 C15 H15 118.9(12) . . ?
C15 C16 C17 121.7(2) . . ?
C15 C16 H16 119.2(12) . . ?
C17 C16 H16 119.1(12) . . ?
C16 C17 C12 117.98(18) . . ?
C16 C17 C18 121.50(18) . . ?
C12 C17 C18 120.51(16) . . ?
C23 C18 C19 117.74(18) . . ?
C23 C18 C17 117.97(16) . . ?
C19 C18 C17 124.29(17) . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.5(11) . . ?
C18 C19 H19 118.5(11) . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.6(11) . . ?
C21 C20 H20 119.3(11) . . ?
C22 C21 C20 119.7(2) . . ?
C22 C21 H21 122.0(12) . . ?
C20 C21 H21 118.3(12) . . ?
C21 C22 C23 121.7(2) . . ?
C21 C22 H22 120.8(11) . . ?
C23 C22 H22 117.5(11) . . ?
C18 C23 C22 118.95(18) . . ?
C18 C23 C24 119.58(17) . . ?
C22 C23 C24 121.47(18) . . ?
C11 C24 C23 123.95(18) . . ?
C11 C24 H24 120.3(11) . . ?
C23 C24 H24 115.6(11) . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        23.99
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.021