# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Zhenfeng Xi'
_publ_contact_author_email       ZFXI@PKU.EDU.CN

_publ_section_title              
;
Zirconocene-Mediated Ligand-Switched Selective
Cleavage of Active and Inert Carbon-Carbon Bonds in Allylcyclopropanes
;
loop_
_publ_author_name
'Zhenfeng Xi'
'Liang Deng'
'Qian Luo'
'Hailin Wang'
'Chao Wang'
'Jun Yan'

# Attachment 'A for revised B908803B.CIF'

data_a
_database_code_depnum_ccdc_archive 'CCDC 730462'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   14.631(3)
_cell_length_b                   12.773(3)
_cell_length_c                   9.3737(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.93(3)
_cell_angle_gamma                90.00
_cell_volume                     1486.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5430
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption
Correction based on Fourier Series
Approximation.Rigaku Corporation,Tokyo,
Japan.
;

_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  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5430
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1699
_reflns_number_gt                1019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
SC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.
;
_computing_cell_refinement       
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381 USA.
;
_computing_data_reduction        
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_solution    
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_refinement  
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the Refinement of Crystal Structure,
University of Gottingen, Germany.
;
_computing_molecular_graphics    
;
Interactive Molecular Graphics XP, Virsion
4.2 for MSDOS (1990), Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin,
USA.
;
_computing_publication_material  
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the refinement of Crystal Structure,
University of Gottingen, Germany.
;

_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 w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0186(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_number_reflns         1699
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
O O 0.0978(2) 0.35972(19) -0.4108(3) 0.0963(8) Uani 1 1 d . . .
C1 C 0.2553(2) 0.25056(19) 0.0020(3) 0.0501(7) Uani 1 1 d . . .
C2 C 0.3279(2) 0.1617(2) 0.0148(3) 0.0582(7) Uani 1 1 d . . .
H2A H 0.3022 0.1165 -0.0824 0.070 Uiso 1 1 calc R . .
H2B H 0.4049 0.1744 0.0774 0.070 Uiso 1 1 calc R . .
C3 C 0.27364(18) 0.15351(19) 0.1124(3) 0.0463(6) Uani 1 1 d . . .
C4 C 0.34069(19) 0.16286(19) 0.3003(3) 0.0486(6) Uani 1 1 d . . .
C5 C 0.3151(2) 0.2338(2) 0.3861(4) 0.0576(7) Uani 1 1 d . . .
H5 H 0.2579 0.2799 0.3272 0.069 Uiso 1 1 calc R . .
C6 C 0.3755(3) 0.2354(3) 0.5605(4) 0.0734(9) Uani 1 1 d . . .
H6 H 0.3586 0.2835 0.6175 0.088 Uiso 1 1 calc R . .
C7 C 0.4594(3) 0.1678(3) 0.6502(4) 0.0811(10) Uani 1 1 d . . .
H7 H 0.4988 0.1695 0.7671 0.097 Uiso 1 1 calc R . .
C8 C 0.4844(3) 0.0983(3) 0.5670(4) 0.0783(10) Uani 1 1 d . . .
H8 H 0.5414 0.0521 0.6271 0.094 Uiso 1 1 calc R . .
C9 C 0.4260(2) 0.0955(2) 0.3936(4) 0.0618(8) Uani 1 1 d . . .
H9 H 0.4444 0.0474 0.3385 0.074 Uiso 1 1 calc R . .
C10 C 0.1824(2) 0.07603(18) 0.0539(3) 0.0460(6) Uani 1 1 d . . .
C11 C 0.0916(2) 0.1005(2) 0.0584(4) 0.0595(7) Uani 1 1 d . . .
H11 H 0.0850 0.1670 0.0924 0.071 Uiso 1 1 calc R . .
C12 C 0.0112(2) 0.0286(2) 0.0137(4) 0.0663(8) Uani 1 1 d . . .
H12 H -0.0488 0.0467 0.0182 0.080 Uiso 1 1 calc R . .
C13 C 0.0189(3) -0.0696(2) -0.0375(4) 0.0659(9) Uani 1 1 d . . .
H13 H -0.0354 -0.1185 -0.0677 0.079 Uiso 1 1 calc R . .
C14 C 0.1082(3) -0.0951(2) -0.0438(4) 0.0707(9) Uani 1 1 d . . .
H14 H 0.1142 -0.1617 -0.0781 0.085 Uiso 1 1 calc R . .
C15 C 0.1889(3) -0.0223(2) 0.0004(4) 0.0594(7) Uani 1 1 d . . .
H15 H 0.2483 -0.0402 -0.0061 0.071 Uiso 1 1 calc R . .
C16 C 0.3093(2) 0.3491(2) 0.0891(4) 0.0594(7) Uani 1 1 d . . .
H16 H 0.3798 0.3446 0.1802 0.071 Uiso 1 1 calc R . .
C17 C 0.2650(4) 0.4427(3) 0.0474(5) 0.0798(10) Uani 1 1 d . . .
H17A H 0.182(3) 0.455(2) -0.042(5) 0.089(11) Uiso 1 1 d . . .
H17B H 0.304(3) 0.496(3) 0.102(4) 0.078(11) Uiso 1 1 d . . .
C18 C 0.1501(2) 0.2607(2) -0.1626(3) 0.0560(7) Uani 1 1 d . . .
H18A H 0.1189 0.1917 -0.2009 0.067 Uiso 1 1 calc R . .
H18B H 0.1007 0.3018 -0.1459 0.067 Uiso 1 1 calc R . .
C19 C 0.1627(3) 0.3115(3) -0.2944(4) 0.0774(10) Uani 1 1 d . . .
H19 H 0.2295 0.3040 -0.2831 0.093 Uiso 1 1 calc R . .

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
O 0.1095(19) 0.0965(16) 0.0684(16) 0.0263(15) 0.0371(15) 0.0098(16)
C1 0.0493(14) 0.0555(15) 0.0476(17) 0.0011(12) 0.0271(13) -0.0015(12)
C2 0.0493(15) 0.0732(18) 0.0549(18) -0.0031(14) 0.0294(15) 0.0042(14)
C3 0.0445(14) 0.0500(15) 0.0438(15) -0.0040(12) 0.0230(13) -0.0004(12)
C4 0.0493(15) 0.0454(14) 0.0481(15) -0.0015(12) 0.0238(13) -0.0067(12)
C5 0.0697(19) 0.0512(16) 0.0535(18) -0.0073(13) 0.0337(16) -0.0111(13)
C6 0.101(3) 0.064(2) 0.064(2) -0.0193(18) 0.049(2) -0.031(2)
C7 0.096(3) 0.081(2) 0.0458(18) -0.0023(18) 0.0235(19) -0.037(2)
C8 0.070(2) 0.070(2) 0.060(2) 0.0139(18) 0.0102(18) -0.0100(17)
C9 0.0610(17) 0.0548(16) 0.057(2) 0.0020(14) 0.0225(16) -0.0031(14)
C10 0.0432(13) 0.0504(15) 0.0391(15) -0.0015(11) 0.0182(12) -0.0005(12)
C11 0.0589(17) 0.0545(15) 0.072(2) -0.0101(15) 0.0395(16) -0.0033(14)
C12 0.0597(18) 0.0677(19) 0.077(2) -0.0057(15) 0.0398(18) -0.0055(15)
C13 0.069(2) 0.0613(18) 0.0599(19) -0.0086(15) 0.0293(16) -0.0189(15)
C14 0.084(2) 0.0529(17) 0.073(2) -0.0152(15) 0.0404(19) -0.0065(17)
C15 0.0649(17) 0.0527(16) 0.0628(18) -0.0126(14) 0.0351(15) -0.0015(14)
C16 0.0577(17) 0.0640(18) 0.0565(18) 0.0026(14) 0.0302(15) -0.0070(15)
C17 0.087(3) 0.059(2) 0.089(3) -0.004(2) 0.043(2) -0.011(2)
C18 0.0512(16) 0.0657(17) 0.0457(17) 0.0051(12) 0.0221(14) -0.0001(13)
C19 0.066(2) 0.110(3) 0.054(2) 0.007(2) 0.0301(17) 0.000(2)

_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
O C19 1.173(3) . ?
C1 C16 1.481(4) . ?
C1 C18 1.502(3) . ?
C1 C2 1.516(4) . ?
C1 C3 1.545(4) . ?
C2 C3 1.500(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.501(3) . ?
C3 C10 1.513(3) . ?
C4 C9 1.381(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.354(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.375(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.317(4) . ?
C16 H16 0.9300 . ?
C17 H17A 1.06(4) . ?
C17 H17B 0.86(4) . ?
C18 C19 1.491(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9300 . ?

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
C16 C1 C18 116.8(2) . . ?
C16 C1 C2 116.5(2) . . ?
C18 C1 C2 116.2(2) . . ?
C16 C1 C3 117.4(2) . . ?
C18 C1 C3 118.5(2) . . ?
C2 C1 C3 58.68(16) . . ?
C3 C2 C1 61.63(16) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C10 118.4(2) . . ?
C4 C3 C10 112.4(2) . . ?
C2 C3 C1 59.69(17) . . ?
C4 C3 C1 119.8(2) . . ?
C10 C3 C1 118.4(2) . . ?
C9 C4 C5 118.0(2) . . ?
C9 C4 C3 120.3(2) . . ?
C5 C4 C3 121.5(2) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C15 C10 C11 118.0(2) . . ?
C15 C10 C3 120.8(2) . . ?
C11 C10 C3 121.2(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.6(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C1 125.0(3) . . ?
C17 C16 H16 117.5 . . ?
C1 C16 H16 117.5 . . ?
C16 C17 H17A 122.9(17) . . ?
C16 C17 H17B 119(2) . . ?
H17A C17 H17B 118(3) . . ?
C19 C18 C1 112.3(2) . . ?
C19 C18 H18A 109.1 . . ?
C1 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C1 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O C19 C18 127.2(3) . . ?
O C19 H19 116.4 . . ?
C18 C19 H19 116.4 . . ?

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
C16 C1 C2 C3 107.3(3) . . . . ?
C18 C1 C2 C3 -108.9(2) . . . . ?
C1 C2 C3 C4 -109.6(3) . . . . ?
C1 C2 C3 C10 108.0(2) . . . . ?
C16 C1 C3 C2 -105.9(3) . . . . ?
C18 C1 C3 C2 104.9(3) . . . . ?
C16 C1 C3 C4 2.1(4) . . . . ?
C18 C1 C3 C4 -147.1(2) . . . . ?
C2 C1 C3 C4 108.0(3) . . . . ?
C16 C1 C3 C10 146.1(2) . . . . ?
C18 C1 C3 C10 -3.2(3) . . . . ?
C2 C1 C3 C10 -108.1(3) . . . . ?
C2 C3 C4 C9 -57.5(3) . . . . ?
C10 C3 C4 C9 87.0(3) . . . . ?
C1 C3 C4 C9 -127.1(3) . . . . ?
C2 C3 C4 C5 126.9(3) . . . . ?
C10 C3 C4 C5 -88.6(3) . . . . ?
C1 C3 C4 C5 57.3(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C6 176.1(2) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C4 -0.2(5) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C3 C4 C9 C8 -175.8(2) . . . . ?
C2 C3 C10 C15 41.8(4) . . . . ?
C4 C3 C10 C15 -102.9(3) . . . . ?
C1 C3 C10 C15 110.7(3) . . . . ?
C2 C3 C10 C11 -140.6(3) . . . . ?
C4 C3 C10 C11 74.7(3) . . . . ?
C1 C3 C10 C11 -71.8(3) . . . . ?
C15 C10 C11 C12 1.1(4) . . . . ?
C3 C10 C11 C12 -176.6(3) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C3 C10 C15 C14 176.2(3) . . . . ?
C13 C14 C15 C10 1.0(5) . . . . ?
C18 C1 C16 C17 11.0(4) . . . . ?
C2 C1 C16 C17 154.5(3) . . . . ?
C3 C1 C16 C17 -138.8(3) . . . . ?
C16 C1 C18 C19 65.1(3) . . . . ?
C2 C1 C18 C19 -78.5(3) . . . . ?
C3 C1 C18 C19 -145.4(3) . . . . ?
C1 C18 C19 O -153.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.043