# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                G.Kehr
_publ_contact_author_name        G.Kehr
_publ_contact_author_email       kehrald@uni-muenster.de

data_erk6658
_database_code_depnum_ccdc_archive 'CCDC 898557'
#TrackingRef '- erk6658.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 Zr'
_chemical_formula_weight         345.62

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'
Zr Zr -2.9673 0.5597 '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                   16.5305(5)
_cell_length_b                   8.3871(3)
_cell_length_c                   25.2496(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0520(10)
_cell_angle_gamma                90.00
_cell_volume                     3380.57(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3946
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16247
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         28.15
_reflns_number_total             4085
_reflns_number_gt                3355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.

The hydrogens at C11, C13 and C14 atoms were refined freely.
;

_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^)+(0.0354P)^2^+5.1992P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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
Zr1 Zr 0.101261(14) 0.50648(2) 0.133934(8) 0.03559(9) Uani 1 1 d . . .
C1 C 0.1819(2) 0.5324(4) 0.23309(12) 0.0645(8) Uani 1 1 d . . .
H1 H 0.1686 0.4611 0.2583 0.077 Uiso 1 1 calc R . .
C2 C 0.2416(2) 0.5094(4) 0.20499(12) 0.0569(8) Uani 1 1 d . . .
H2 H 0.2759 0.4188 0.2075 0.068 Uiso 1 1 calc R . .
C3 C 0.24322(18) 0.6406(4) 0.17237(12) 0.0592(7) Uani 1 1 d . . .
H3 H 0.2783 0.6543 0.1488 0.071 Uiso 1 1 calc R . .
C4 C 0.1837(2) 0.7496(4) 0.18039(14) 0.0669(9) Uani 1 1 d . . .
H4 H 0.1725 0.8504 0.1638 0.080 Uiso 1 1 calc R . .
C5 C 0.1438(2) 0.6821(5) 0.21751(13) 0.0728(10) Uani 1 1 d . . .
H5 H 0.1000 0.7276 0.2298 0.087 Uiso 1 1 calc R . .
C6 C 0.0528(3) 0.2709(4) 0.18171(16) 0.0871(13) Uani 1 1 d . . .
H6 H 0.0507 0.2868 0.2182 0.105 Uiso 1 1 calc R . .
C7 C 0.1200(3) 0.2168(4) 0.16553(17) 0.0797(11) Uani 1 1 d . . .
H7 H 0.1720 0.1880 0.1890 0.096 Uiso 1 1 calc R . .
C8 C 0.0998(3) 0.2111(4) 0.11028(17) 0.0739(10) Uani 1 1 d . . .
H8 H 0.1359 0.1790 0.0890 0.089 Uiso 1 1 calc R . .
C9 C 0.0192(3) 0.2590(4) 0.09028(15) 0.0779(11) Uani 1 1 d . . .
H9 H -0.0102 0.2643 0.0531 0.094 Uiso 1 1 calc R . .
C10 C -0.0127(2) 0.2991(4) 0.1351(2) 0.0929(14) Uani 1 1 d . . .
H10 H -0.0666 0.3370 0.1339 0.112 Uiso 1 1 calc R . .
C11 C 0.12701(19) 0.5244(3) 0.04824(11) 0.0451(6) Uani 1 1 d . . .
H11A H 0.172(2) 0.500(3) 0.0356(12) 0.050(9) Uiso 1 1 d . . .
H11B H 0.079(2) 0.463(4) 0.0344(12) 0.051(8) Uiso 1 1 d . . .
C12 C 0.11263(15) 0.6905(3) 0.05586(10) 0.0415(5) Uani 1 1 d . . .
C13 C 0.04797(15) 0.7480(3) 0.07630(9) 0.0376(5) Uani 1 1 d . . .
H13 H 0.0517(16) 0.856(3) 0.0862(10) 0.039(7) Uiso 1 1 d . . .
C14 C -0.01593(14) 0.6587(3) 0.09276(10) 0.0376(5) Uani 1 1 d . . .
H14 H -0.0333(17) 0.563(4) 0.0711(11) 0.050(8) Uiso 1 1 d . . .
C15 C 0.17823(19) 0.8066(4) 0.04792(13) 0.0602(8) Uani 1 1 d . . .
H15A H 0.1705 0.8263 0.0091 0.090 Uiso 1 1 calc R . .
H15B H 0.2335 0.7620 0.0633 0.090 Uiso 1 1 calc R . .
H15C H 0.1729 0.9060 0.0663 0.090 Uiso 1 1 calc R . .
C16 C -0.08827(16) 0.7526(3) 0.10555(11) 0.0485(6) Uani 1 1 d . . .
C17 C -0.05732(19) 0.8669(4) 0.15380(13) 0.0615(8) Uani 1 1 d . . .
H17A H -0.0162 0.9392 0.1458 0.092 Uiso 1 1 calc R . .
H17B H -0.0318 0.8063 0.1866 0.092 Uiso 1 1 calc R . .
H17C H -0.1042 0.9276 0.1596 0.092 Uiso 1 1 calc R . .
C18 C -0.1511(2) 0.6382(5) 0.11904(18) 0.0854(12) Uani 1 1 d . . .
H18A H -0.1247 0.5795 0.1521 0.128 Uiso 1 1 calc R . .
H18B H -0.1703 0.5641 0.0889 0.128 Uiso 1 1 calc R . .
H18C H -0.1984 0.6977 0.1247 0.128 Uiso 1 1 calc R . .
C19 C -0.1326(2) 0.8512(5) 0.05487(15) 0.0790(10) Uani 1 1 d . . .
H19A H -0.1790 0.9094 0.0626 0.118 Uiso 1 1 calc R . .
H19B H -0.1537 0.7805 0.0240 0.118 Uiso 1 1 calc R . .
H19C H -0.0932 0.9259 0.0461 0.118 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
Zr1 0.03948(14) 0.03221(14) 0.03091(13) -0.00254(8) 0.00162(9) 0.00297(9)
C1 0.068(2) 0.082(2) 0.0342(13) -0.0047(14) -0.0021(13) -0.0015(17)
C2 0.0537(16) 0.0630(19) 0.0421(15) -0.0038(12) -0.0088(12) 0.0121(13)
C3 0.0477(15) 0.0674(19) 0.0526(16) -0.0051(14) -0.0048(12) -0.0072(14)
C4 0.068(2) 0.0461(16) 0.0645(19) -0.0143(14) -0.0216(16) -0.0022(15)
C5 0.0576(18) 0.096(3) 0.0536(17) -0.0408(18) -0.0061(14) 0.0120(18)
C6 0.144(4) 0.058(2) 0.069(2) 0.0009(17) 0.045(3) -0.028(2)
C7 0.093(3) 0.0429(17) 0.087(3) 0.0207(17) -0.006(2) 0.0001(17)
C8 0.095(3) 0.0342(15) 0.095(3) -0.0075(15) 0.031(2) 0.0024(16)
C9 0.099(3) 0.0431(17) 0.070(2) 0.0047(15) -0.016(2) -0.0248(18)
C10 0.061(2) 0.0375(16) 0.185(5) 0.015(2) 0.041(3) -0.0071(15)
C11 0.0456(14) 0.0516(15) 0.0380(13) -0.0067(11) 0.0108(11) 0.0082(12)
C12 0.0371(12) 0.0485(14) 0.0385(12) 0.0029(10) 0.0090(9) 0.0031(10)
C13 0.0375(11) 0.0351(12) 0.0384(12) 0.0017(9) 0.0068(9) 0.0036(10)
C14 0.0334(11) 0.0378(12) 0.0400(12) -0.0017(10) 0.0065(9) 0.0033(9)
C15 0.0565(17) 0.0596(18) 0.073(2) 0.0074(15) 0.0317(15) -0.0015(14)
C16 0.0369(12) 0.0488(15) 0.0617(16) -0.0032(12) 0.0162(11) 0.0056(11)
C17 0.0574(17) 0.0569(17) 0.077(2) -0.0152(15) 0.0289(15) 0.0065(14)
C18 0.0551(19) 0.081(3) 0.136(3) -0.019(2) 0.054(2) -0.0143(18)
C19 0.0533(18) 0.087(3) 0.090(2) 0.007(2) 0.0067(17) 0.0323(18)

_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
Zr1 C11 2.316(3) . ?
Zr1 C14 2.327(2) . ?
Zr1 C13 2.517(2) . ?
Zr1 C5 2.519(3) . ?
Zr1 C1 2.522(3) . ?
Zr1 C2 2.538(3) . ?
Zr1 C8 2.547(3) . ?
Zr1 C12 2.549(2) . ?
Zr1 C6 2.550(3) . ?
Zr1 C7 2.551(3) . ?
Zr1 C3 2.556(3) . ?
Zr1 C4 2.562(3) . ?
C1 C2 1.371(5) . ?
C1 C5 1.414(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.356(6) . ?
C6 C10 1.398(6) . ?
C6 H6 0.9400 . ?
C7 C8 1.348(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.358(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.406(6) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.435(4) . ?
C11 H11A 0.90(3) . ?
C11 H11B 0.93(3) . ?
C12 C13 1.389(3) . ?
C12 C15 1.509(4) . ?
C13 C14 1.441(3) . ?
C13 H13 0.94(3) . ?
C14 C16 1.535(3) . ?
C14 H14 0.97(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C18 1.516(4) . ?
C16 C17 1.530(4) . ?
C16 C19 1.540(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

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
C11 Zr1 C14 83.15(9) . . ?
C11 Zr1 C13 61.92(9) . . ?
C14 Zr1 C13 34.34(8) . . ?
C11 Zr1 C5 131.73(13) . . ?
C14 Zr1 C5 94.16(10) . . ?
C13 Zr1 C5 89.62(11) . . ?
C11 Zr1 C1 138.07(11) . . ?
C14 Zr1 C1 124.08(10) . . ?
C13 Zr1 C1 121.34(10) . . ?
C5 Zr1 C1 32.57(11) . . ?
C11 Zr1 C2 107.68(11) . . ?
C14 Zr1 C2 144.35(9) . . ?
C13 Zr1 C2 121.31(9) . . ?
C5 Zr1 C2 52.92(10) . . ?
C1 Zr1 C2 31.44(11) . . ?
C11 Zr1 C8 80.60(11) . . ?
C14 Zr1 C8 118.21(11) . . ?
C13 Zr1 C8 131.83(11) . . ?
C5 Zr1 C8 138.47(13) . . ?
C1 Zr1 C8 106.67(12) . . ?
C2 Zr1 C8 97.25(11) . . ?
C11 Zr1 C12 33.89(9) . . ?
C14 Zr1 C12 62.76(8) . . ?
C13 Zr1 C12 31.81(8) . . ?
C5 Zr1 C12 103.48(12) . . ?
C1 Zr1 C12 126.12(10) . . ?
C2 Zr1 C12 107.67(9) . . ?
C8 Zr1 C12 113.94(11) . . ?
C11 Zr1 C6 130.44(11) . . ?
C14 Zr1 C6 108.01(14) . . ?
C13 Zr1 C6 142.34(14) . . ?
C5 Zr1 C6 96.34(13) . . ?
C1 Zr1 C6 75.34(13) . . ?
C2 Zr1 C6 90.84(14) . . ?
C8 Zr1 C6 51.12(12) . . ?
C12 Zr1 C6 158.51(12) . . ?
C11 Zr1 C7 108.49(13) . . ?
C14 Zr1 C7 132.95(11) . . ?
C13 Zr1 C7 160.64(11) . . ?
C5 Zr1 C7 108.06(14) . . ?
C1 Zr1 C7 77.39(13) . . ?
C2 Zr1 C7 76.92(11) . . ?
C8 Zr1 C7 30.67(12) . . ?
C12 Zr1 C7 142.32(12) . . ?
C6 Zr1 C7 30.84(13) . . ?
C11 Zr1 C3 87.30(11) . . ?
C14 Zr1 C3 120.26(10) . . ?
C13 Zr1 C3 90.82(9) . . ?
C5 Zr1 C3 52.80(11) . . ?
C1 Zr1 C3 52.31(11) . . ?
C2 Zr1 C3 31.41(10) . . ?
C8 Zr1 C3 117.96(12) . . ?
C12 Zr1 C3 77.42(9) . . ?
C6 Zr1 C3 122.11(14) . . ?
C7 Zr1 C3 106.00(12) . . ?
C11 Zr1 C4 99.86(12) . . ?
C14 Zr1 C4 92.87(9) . . ?
C13 Zr1 C4 71.86(9) . . ?
C5 Zr1 C4 31.94(12) . . ?
C1 Zr1 C4 52.81(11) . . ?
C2 Zr1 C4 52.31(10) . . ?
C8 Zr1 C4 148.55(12) . . ?
C12 Zr1 C4 74.61(10) . . ?
C6 Zr1 C4 126.53(12) . . ?
C7 Zr1 C4 127.46(11) . . ?
C3 Zr1 C4 31.66(10) . . ?
C2 C1 C5 108.0(3) . . ?
C2 C1 Zr1 74.92(17) . . ?
C5 C1 Zr1 73.61(16) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Zr1 C1 H1 117.5 . . ?
C1 C2 C3 109.0(3) . . ?
C1 C2 Zr1 73.64(17) . . ?
C3 C2 Zr1 75.01(16) . . ?
C1 C2 H2 125.5 . . ?
C3 C2 H2 125.5 . . ?
Zr1 C2 H2 117.7 . . ?
C2 C3 C4 108.2(3) . . ?
C2 C3 Zr1 73.57(17) . . ?
C4 C3 Zr1 74.41(16) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Zr1 C3 H3 118.1 . . ?
C3 C4 C5 107.7(3) . . ?
C3 C4 Zr1 73.94(17) . . ?
C5 C4 Zr1 72.35(17) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Zr1 C4 H4 119.5 . . ?
C4 C5 C1 107.0(3) . . ?
C4 C5 Zr1 75.71(16) . . ?
C1 C5 Zr1 73.82(16) . . ?
C4 C5 H5 126.5 . . ?
C1 C5 H5 126.5 . . ?
Zr1 C5 H5 116.2 . . ?
C7 C6 C10 108.6(4) . . ?
C7 C6 Zr1 74.6(2) . . ?
C10 C6 Zr1 74.9(2) . . ?
C7 C6 H6 125.7 . . ?
C10 C6 H6 125.7 . . ?
Zr1 C6 H6 116.7 . . ?
C8 C7 C6 108.8(4) . . ?
C8 C7 Zr1 74.50(18) . . ?
C6 C7 Zr1 74.5(2) . . ?
C8 C7 H7 125.6 . . ?
C6 C7 H7 125.6 . . ?
Zr1 C7 H7 117.3 . . ?
C7 C8 C9 109.2(4) . . ?
C7 C8 Zr1 74.83(19) . . ?
C9 C8 Zr1 75.40(19) . . ?
C7 C8 H8 125.4 . . ?
C9 C8 H8 125.4 . . ?
Zr1 C8 H8 116.3 . . ?
C8 C9 C10 108.0(3) . . ?
C8 C9 Zr1 73.80(19) . . ?
C10 C9 Zr1 74.20(19) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Zr1 C9 H9 118.0 . . ?
C6 C10 C9 105.5(3) . . ?
C6 C10 Zr1 73.4(2) . . ?
C9 C10 Zr1 74.02(19) . . ?
C6 C10 H10 127.3 . . ?
C9 C10 H10 127.3 . . ?
Zr1 C10 H10 117.6 . . ?
C12 C11 Zr1 81.99(15) . . ?
C12 C11 H11A 116.6(17) . . ?
Zr1 C11 H11A 133.0(19) . . ?
C12 C11 H11B 115.8(19) . . ?
Zr1 C11 H11B 88.4(18) . . ?
H11A C11 H11B 116(3) . . ?
C13 C12 C11 123.9(2) . . ?
C13 C12 C15 118.3(2) . . ?
C11 C12 C15 117.3(2) . . ?
C13 C12 Zr1 72.81(14) . . ?
C11 C12 Zr1 64.12(14) . . ?
C15 C12 Zr1 133.90(18) . . ?
C12 C13 C14 128.2(2) . . ?
C12 C13 Zr1 75.38(14) . . ?
C14 C13 Zr1 65.63(13) . . ?
C12 C13 H13 115.6(15) . . ?
C14 C13 H13 115.3(15) . . ?
Zr1 C13 H13 129.4(15) . . ?
C13 C14 C16 117.6(2) . . ?
C13 C14 Zr1 80.03(13) . . ?
C16 C14 Zr1 142.29(17) . . ?
C13 C14 H14 113.4(17) . . ?
C16 C14 H14 114.2(17) . . ?
Zr1 C14 H14 83.7(17) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C17 108.9(3) . . ?
C18 C16 C14 109.8(2) . . ?
C17 C16 C14 111.8(2) . . ?
C18 C16 C19 108.7(3) . . ?
C17 C16 C19 108.3(3) . . ?
C14 C16 C19 109.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C11 Zr1 C1 C2 -18.2(3) . . . . ?
C14 Zr1 C1 C2 -140.75(18) . . . . ?
C13 Zr1 C1 C2 -99.8(2) . . . . ?
C5 Zr1 C1 C2 -114.4(3) . . . . ?
C8 Zr1 C1 C2 76.3(2) . . . . ?
C12 Zr1 C1 C2 -61.7(2) . . . . ?
C6 Zr1 C1 C2 117.2(2) . . . . ?
C7 Zr1 C1 C2 85.5(2) . . . . ?
C3 Zr1 C1 C2 -36.51(19) . . . . ?
C4 Zr1 C1 C2 -76.7(2) . . . . ?
C11 Zr1 C1 C5 96.2(3) . . . . ?
C14 Zr1 C1 C5 -26.3(3) . . . . ?
C13 Zr1 C1 C5 14.6(3) . . . . ?
C2 Zr1 C1 C5 114.4(3) . . . . ?
C8 Zr1 C1 C5 -169.3(2) . . . . ?
C12 Zr1 C1 C5 52.7(3) . . . . ?
C6 Zr1 C1 C5 -128.4(3) . . . . ?
C7 Zr1 C1 C5 -160.1(3) . . . . ?
C3 Zr1 C1 C5 77.9(2) . . . . ?
C4 Zr1 C1 C5 37.7(2) . . . . ?
C5 C1 C2 C3 0.6(3) . . . . ?
Zr1 C1 C2 C3 67.3(2) . . . . ?
C5 C1 C2 Zr1 -66.7(2) . . . . ?
C11 Zr1 C2 C1 167.3(2) . . . . ?
C14 Zr1 C2 C1 64.0(3) . . . . ?
C13 Zr1 C2 C1 99.9(2) . . . . ?
C5 Zr1 C2 C1 37.9(2) . . . . ?
C8 Zr1 C2 C1 -110.3(2) . . . . ?
C12 Zr1 C2 C1 131.7(2) . . . . ?
C6 Zr1 C2 C1 -59.4(2) . . . . ?
C7 Zr1 C2 C1 -87.1(2) . . . . ?
C3 Zr1 C2 C1 115.4(3) . . . . ?
C4 Zr1 C2 C1 78.4(2) . . . . ?
C11 Zr1 C2 C3 51.9(2) . . . . ?
C14 Zr1 C2 C3 -51.4(3) . . . . ?
C13 Zr1 C2 C3 -15.5(2) . . . . ?
C5 Zr1 C2 C3 -77.5(2) . . . . ?
C1 Zr1 C2 C3 -115.4(3) . . . . ?
C8 Zr1 C2 C3 134.3(2) . . . . ?
C12 Zr1 C2 C3 16.3(2) . . . . ?
C6 Zr1 C2 C3 -174.8(2) . . . . ?
C7 Zr1 C2 C3 157.4(2) . . . . ?
C4 Zr1 C2 C3 -36.99(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
Zr1 C2 C3 C4 66.92(19) . . . . ?
C1 C2 C3 Zr1 -66.4(2) . . . . ?
C11 Zr1 C3 C2 -131.4(2) . . . . ?
C14 Zr1 C3 C2 148.19(18) . . . . ?
C13 Zr1 C3 C2 166.81(19) . . . . ?
C5 Zr1 C3 C2 77.9(2) . . . . ?
C1 Zr1 C3 C2 36.53(19) . . . . ?
C8 Zr1 C3 C2 -53.5(2) . . . . ?
C12 Zr1 C3 C2 -164.1(2) . . . . ?
C6 Zr1 C3 C2 6.1(2) . . . . ?
C7 Zr1 C3 C2 -22.9(2) . . . . ?
C4 Zr1 C3 C2 114.9(3) . . . . ?
C11 Zr1 C3 C4 113.8(2) . . . . ?
C14 Zr1 C3 C4 33.3(2) . . . . ?
C13 Zr1 C3 C4 51.9(2) . . . . ?
C5 Zr1 C3 C4 -37.0(2) . . . . ?
C1 Zr1 C3 C4 -78.3(2) . . . . ?
C2 Zr1 C3 C4 -114.9(3) . . . . ?
C8 Zr1 C3 C4 -168.4(2) . . . . ?
C12 Zr1 C3 C4 81.0(2) . . . . ?
C6 Zr1 C3 C4 -108.7(2) . . . . ?
C7 Zr1 C3 C4 -137.8(2) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
Zr1 C3 C4 C5 65.0(2) . . . . ?
C2 C3 C4 Zr1 -66.4(2) . . . . ?
C11 Zr1 C4 C3 -68.1(2) . . . . ?
C14 Zr1 C4 C3 -151.6(2) . . . . ?
C13 Zr1 C4 C3 -124.1(2) . . . . ?
C5 Zr1 C4 C3 115.1(3) . . . . ?
C1 Zr1 C4 C3 76.6(2) . . . . ?
C2 Zr1 C4 C3 36.70(18) . . . . ?
C8 Zr1 C4 C3 20.0(4) . . . . ?
C12 Zr1 C4 C3 -90.9(2) . . . . ?
C6 Zr1 C4 C3 93.4(3) . . . . ?
C7 Zr1 C4 C3 54.5(3) . . . . ?
C11 Zr1 C4 C5 176.80(19) . . . . ?
C14 Zr1 C4 C5 93.3(2) . . . . ?
C13 Zr1 C4 C5 120.8(2) . . . . ?
C1 Zr1 C4 C5 -38.51(19) . . . . ?
C2 Zr1 C4 C5 -78.4(2) . . . . ?
C8 Zr1 C4 C5 -95.1(3) . . . . ?
C12 Zr1 C4 C5 154.0(2) . . . . ?
C6 Zr1 C4 C5 -21.7(3) . . . . ?
C7 Zr1 C4 C5 -60.6(3) . . . . ?
C3 Zr1 C4 C5 -115.1(3) . . . . ?
C3 C4 C5 C1 1.7(3) . . . . ?
Zr1 C4 C5 C1 67.7(2) . . . . ?
C3 C4 C5 Zr1 -66.01(19) . . . . ?
C2 C1 C5 C4 -1.4(3) . . . . ?
Zr1 C1 C5 C4 -69.04(19) . . . . ?
C2 C1 C5 Zr1 67.6(2) . . . . ?
C11 Zr1 C5 C4 -4.2(3) . . . . ?
C14 Zr1 C5 C4 -88.76(19) . . . . ?
C13 Zr1 C5 C4 -54.69(19) . . . . ?
C1 Zr1 C5 C4 112.9(3) . . . . ?
C2 Zr1 C5 C4 76.3(2) . . . . ?
C8 Zr1 C5 C4 128.4(2) . . . . ?
C12 Zr1 C5 C4 -25.8(2) . . . . ?
C6 Zr1 C5 C4 162.6(2) . . . . ?
C7 Zr1 C5 C4 133.3(2) . . . . ?
C3 Zr1 C5 C4 36.63(18) . . . . ?
C11 Zr1 C5 C1 -117.1(2) . . . . ?
C14 Zr1 C5 C1 158.4(2) . . . . ?
C13 Zr1 C5 C1 -167.6(2) . . . . ?
C2 Zr1 C5 C1 -36.5(2) . . . . ?
C8 Zr1 C5 C1 15.5(3) . . . . ?
C12 Zr1 C5 C1 -138.7(2) . . . . ?
C6 Zr1 C5 C1 49.7(3) . . . . ?
C7 Zr1 C5 C1 20.5(3) . . . . ?
C3 Zr1 C5 C1 -76.2(2) . . . . ?
C4 Zr1 C5 C1 -112.9(3) . . . . ?
C11 Zr1 C6 C7 52.1(3) . . . . ?
C14 Zr1 C6 C7 148.5(2) . . . . ?
C13 Zr1 C6 C7 147.4(2) . . . . ?
C5 Zr1 C6 C7 -115.0(3) . . . . ?
C1 Zr1 C6 C7 -89.9(3) . . . . ?
C2 Zr1 C6 C7 -62.2(3) . . . . ?
C8 Zr1 C6 C7 36.4(2) . . . . ?
C12 Zr1 C6 C7 87.7(5) . . . . ?
C3 Zr1 C6 C7 -65.4(3) . . . . ?
C4 Zr1 C6 C7 -103.6(2) . . . . ?
C11 Zr1 C6 C10 -62.5(3) . . . . ?
C14 Zr1 C6 C10 33.9(3) . . . . ?
C13 Zr1 C6 C10 32.8(3) . . . . ?
C5 Zr1 C6 C10 130.4(3) . . . . ?
C1 Zr1 C6 C10 155.5(3) . . . . ?
C2 Zr1 C6 C10 -176.8(3) . . . . ?
C8 Zr1 C6 C10 -78.2(3) . . . . ?
C12 Zr1 C6 C10 -26.9(5) . . . . ?
C7 Zr1 C6 C10 -114.6(4) . . . . ?
C3 Zr1 C6 C10 180.0(2) . . . . ?
C4 Zr1 C6 C10 141.8(2) . . . . ?
C10 C6 C7 C8 0.6(4) . . . . ?
Zr1 C6 C7 C8 -67.2(2) . . . . ?
C10 C6 C7 Zr1 67.8(2) . . . . ?
C11 Zr1 C7 C8 -25.7(3) . . . . ?
C14 Zr1 C7 C8 72.3(3) . . . . ?
C13 Zr1 C7 C8 31.3(5) . . . . ?
C5 Zr1 C7 C8 -173.6(2) . . . . ?
C1 Zr1 C7 C8 -162.5(3) . . . . ?
C2 Zr1 C7 C8 -130.2(3) . . . . ?
C12 Zr1 C7 C8 -28.2(4) . . . . ?
C6 Zr1 C7 C8 115.1(4) . . . . ?
C3 Zr1 C7 C8 -118.2(3) . . . . ?
C4 Zr1 C7 C8 -144.6(2) . . . . ?
C11 Zr1 C7 C6 -140.7(3) . . . . ?
C14 Zr1 C7 C6 -42.7(3) . . . . ?
C13 Zr1 C7 C6 -83.8(5) . . . . ?
C5 Zr1 C7 C6 71.4(3) . . . . ?
C1 Zr1 C7 C6 82.5(3) . . . . ?
C2 Zr1 C7 C6 114.7(3) . . . . ?
C8 Zr1 C7 C6 -115.1(4) . . . . ?
C12 Zr1 C7 C6 -143.2(2) . . . . ?
C3 Zr1 C7 C6 126.7(2) . . . . ?
C4 Zr1 C7 C6 100.4(3) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
Zr1 C7 C8 C9 -68.2(2) . . . . ?
C6 C7 C8 Zr1 67.2(3) . . . . ?
C11 Zr1 C8 C7 155.4(3) . . . . ?
C14 Zr1 C8 C7 -127.7(3) . . . . ?
C13 Zr1 C8 C7 -166.7(2) . . . . ?
C5 Zr1 C8 C7 9.2(4) . . . . ?
C1 Zr1 C8 C7 17.9(3) . . . . ?
C2 Zr1 C8 C7 48.6(3) . . . . ?
C12 Zr1 C8 C7 161.6(2) . . . . ?
C6 Zr1 C8 C7 -36.6(3) . . . . ?
C3 Zr1 C8 C7 73.6(3) . . . . ?
C4 Zr1 C8 C7 61.8(4) . . . . ?
C11 Zr1 C8 C9 -89.6(3) . . . . ?
C14 Zr1 C8 C9 -12.7(3) . . . . ?
C13 Zr1 C8 C9 -51.6(3) . . . . ?
C5 Zr1 C8 C9 124.2(3) . . . . ?
C1 Zr1 C8 C9 132.9(3) . . . . ?
C2 Zr1 C8 C9 163.6(2) . . . . ?
C12 Zr1 C8 C9 -83.4(3) . . . . ?
C6 Zr1 C8 C9 78.4(3) . . . . ?
C7 Zr1 C8 C9 115.0(4) . . . . ?
C3 Zr1 C8 C9 -171.4(2) . . . . ?
C4 Zr1 C8 C9 176.9(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
Zr1 C8 C9 C10 -66.9(2) . . . . ?
C7 C8 C9 Zr1 67.8(2) . . . . ?
C11 Zr1 C9 C8 85.5(3) . . . . ?
C14 Zr1 C9 C8 168.9(3) . . . . ?
C13 Zr1 C9 C8 141.7(2) . . . . ?
C5 Zr1 C9 C8 -96.6(3) . . . . ?
C1 Zr1 C9 C8 -59.5(3) . . . . ?
C2 Zr1 C9 C8 -20.4(3) . . . . ?
C12 Zr1 C9 C8 108.2(2) . . . . ?
C6 Zr1 C9 C8 -76.2(3) . . . . ?
C7 Zr1 C9 C8 -36.5(2) . . . . ?
C3 Zr1 C9 C8 14.5(4) . . . . ?
C4 Zr1 C9 C8 -70(4) . . . . ?
C11 Zr1 C9 C10 -159.9(3) . . . . ?
C14 Zr1 C9 C10 -76.6(3) . . . . ?
C13 Zr1 C9 C10 -103.8(2) . . . . ?
C5 Zr1 C9 C10 18.0(4) . . . . ?
C1 Zr1 C9 C10 55.0(3) . . . . ?
C2 Zr1 C9 C10 94.2(3) . . . . ?
C8 Zr1 C9 C10 114.6(3) . . . . ?
C12 Zr1 C9 C10 -137.2(2) . . . . ?
C6 Zr1 C9 C10 38.3(2) . . . . ?
C7 Zr1 C9 C10 78.1(3) . . . . ?
C3 Zr1 C9 C10 129.0(3) . . . . ?
C4 Zr1 C9 C10 45(4) . . . . ?
C7 C6 C10 C9 0.0(4) . . . . ?
Zr1 C6 C10 C9 67.6(2) . . . . ?
C7 C6 C10 Zr1 -67.7(3) . . . . ?
C8 C9 C10 C6 -0.5(4) . . . . ?
Zr1 C9 C10 C6 -67.2(2) . . . . ?
C8 C9 C10 Zr1 66.6(2) . . . . ?
C11 Zr1 C10 C6 133.5(3) . . . . ?
C14 Zr1 C10 C6 -147.5(3) . . . . ?
C13 Zr1 C10 C6 -158.8(2) . . . . ?
C5 Zr1 C10 C6 -57.0(3) . . . . ?
C1 Zr1 C10 C6 -24.4(3) . . . . ?
C2 Zr1 C10 C6 3.8(3) . . . . ?
C8 Zr1 C10 C6 75.7(3) . . . . ?
C12 Zr1 C10 C6 167.8(2) . . . . ?
C7 Zr1 C10 C6 36.4(2) . . . . ?
C3 Zr1 C10 C6 0.0(5) . . . . ?
C4 Zr1 C10 C6 -65.7(3) . . . . ?
C11 Zr1 C10 C9 21.4(3) . . . . ?
C14 Zr1 C10 C9 100.5(3) . . . . ?
C13 Zr1 C10 C9 89.2(2) . . . . ?
C5 Zr1 C10 C9 -169.1(2) . . . . ?
C1 Zr1 C10 C9 -136.5(2) . . . . ?
C2 Zr1 C10 C9 -108.3(3) . . . . ?
C8 Zr1 C10 C9 -36.3(2) . . . . ?
C12 Zr1 C10 C9 55.8(3) . . . . ?
C6 Zr1 C10 C9 -112.0(3) . . . . ?
C7 Zr1 C10 C9 -75.6(2) . . . . ?
C3 Zr1 C10 C9 -112.0(4) . . . . ?
C4 Zr1 C10 C9 -177.73(19) . . . . ?
C14 Zr1 C11 C12 49.62(16) . . . . ?
C13 Zr1 C11 C12 21.08(14) . . . . ?
C5 Zr1 C11 C12 -39.8(2) . . . . ?
C1 Zr1 C11 C12 -85.7(2) . . . . ?
C2 Zr1 C11 C12 -95.54(16) . . . . ?
C8 Zr1 C11 C12 169.78(19) . . . . ?
C6 Zr1 C11 C12 157.5(2) . . . . ?
C7 Zr1 C11 C12 -177.27(17) . . . . ?
C3 Zr1 C11 C12 -71.30(17) . . . . ?
C4 Zr1 C11 C12 -42.12(17) . . . . ?
Zr1 C11 C12 C13 -43.8(2) . . . . ?
Zr1 C11 C12 C15 128.1(2) . . . . ?
C11 Zr1 C12 C13 143.0(2) . . . . ?
C14 Zr1 C12 C13 21.27(14) . . . . ?
C5 Zr1 C12 C13 -66.46(17) . . . . ?
C1 Zr1 C12 C13 -92.58(18) . . . . ?
C2 Zr1 C12 C13 -121.41(15) . . . . ?
C8 Zr1 C12 C13 131.96(17) . . . . ?
C6 Zr1 C12 C13 90.3(4) . . . . ?
C7 Zr1 C12 C13 147.23(19) . . . . ?
C3 Zr1 C12 C13 -112.79(16) . . . . ?
C4 Zr1 C12 C13 -80.27(16) . . . . ?
C14 Zr1 C12 C11 -121.72(18) . . . . ?
C13 Zr1 C12 C11 -143.0(2) . . . . ?
C5 Zr1 C12 C11 150.55(17) . . . . ?
C1 Zr1 C12 C11 124.42(18) . . . . ?
C2 Zr1 C12 C11 95.60(17) . . . . ?
C8 Zr1 C12 C11 -11.0(2) . . . . ?
C6 Zr1 C12 C11 -52.7(4) . . . . ?
C7 Zr1 C12 C11 4.2(3) . . . . ?
C3 Zr1 C12 C11 104.21(18) . . . . ?
C4 Zr1 C12 C11 136.74(18) . . . . ?
C11 Zr1 C12 C15 -103.9(3) . . . . ?
C14 Zr1 C12 C15 134.3(3) . . . . ?
C13 Zr1 C12 C15 113.1(3) . . . . ?
C5 Zr1 C12 C15 46.6(3) . . . . ?
C1 Zr1 C12 C15 20.5(3) . . . . ?
C2 Zr1 C12 C15 -8.3(3) . . . . ?
C8 Zr1 C12 C15 -115.0(3) . . . . ?
C6 Zr1 C12 C15 -156.6(4) . . . . ?
C7 Zr1 C12 C15 -99.7(3) . . . . ?
C3 Zr1 C12 C15 0.3(3) . . . . ?
C4 Zr1 C12 C15 32.8(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C15 C12 C13 C14 -172.7(2) . . . . ?
Zr1 C12 C13 C14 -41.5(2) . . . . ?
C11 C12 C13 Zr1 40.7(2) . . . . ?
C15 C12 C13 Zr1 -131.1(2) . . . . ?
C11 Zr1 C13 C12 -22.36(15) . . . . ?
C14 Zr1 C13 C12 -145.1(2) . . . . ?
C5 Zr1 C13 C12 116.93(17) . . . . ?
C1 Zr1 C13 C12 109.12(17) . . . . ?
C2 Zr1 C13 C12 72.15(17) . . . . ?
C8 Zr1 C13 C12 -65.8(2) . . . . ?
C6 Zr1 C13 C12 -143.16(19) . . . . ?
C7 Zr1 C13 C12 -86.6(4) . . . . ?
C3 Zr1 C13 C12 64.14(16) . . . . ?
C4 Zr1 C13 C12 89.92(17) . . . . ?
C11 Zr1 C13 C14 122.77(17) . . . . ?
C5 Zr1 C13 C14 -97.94(16) . . . . ?
C1 Zr1 C13 C14 -105.75(16) . . . . ?
C2 Zr1 C13 C14 -142.73(15) . . . . ?
C8 Zr1 C13 C14 79.31(19) . . . . ?
C12 Zr1 C13 C14 145.1(2) . . . . ?
C6 Zr1 C13 C14 2.0(2) . . . . ?
C7 Zr1 C13 C14 58.5(4) . . . . ?
C3 Zr1 C13 C14 -150.73(15) . . . . ?
C4 Zr1 C13 C14 -124.96(17) . . . . ?
C12 C13 C14 C16 -170.7(2) . . . . ?
Zr1 C13 C14 C16 144.5(2) . . . . ?
C12 C13 C14 Zr1 44.8(2) . . . . ?
C11 Zr1 C14 C13 -48.35(15) . . . . ?
C5 Zr1 C14 C13 83.22(16) . . . . ?
C1 Zr1 C14 C13 97.08(17) . . . . ?
C2 Zr1 C14 C13 62.6(2) . . . . ?
C8 Zr1 C14 C13 -123.81(16) . . . . ?
C12 Zr1 C14 C13 -19.82(13) . . . . ?
C6 Zr1 C14 C13 -178.74(15) . . . . ?
C7 Zr1 C14 C13 -157.29(18) . . . . ?
C3 Zr1 C14 C13 34.46(17) . . . . ?
C4 Zr1 C14 C13 51.24(16) . . . . ?
C11 Zr1 C14 C16 -171.1(3) . . . . ?
C13 Zr1 C14 C16 -122.8(3) . . . . ?
C5 Zr1 C14 C16 -39.6(3) . . . . ?
C1 Zr1 C14 C16 -25.7(3) . . . . ?
C2 Zr1 C14 C16 -60.2(4) . . . . ?
C8 Zr1 C14 C16 113.4(3) . . . . ?
C12 Zr1 C14 C16 -142.6(3) . . . . ?
C6 Zr1 C14 C16 58.5(3) . . . . ?
C7 Zr1 C14 C16 79.9(3) . . . . ?
C3 Zr1 C14 C16 -88.3(3) . . . . ?
C4 Zr1 C14 C16 -71.5(3) . . . . ?
C13 C14 C16 C18 177.0(3) . . . . ?
Zr1 C14 C16 C18 -72.1(4) . . . . ?
C13 C14 C16 C17 -62.0(3) . . . . ?
Zr1 C14 C16 C17 48.9(4) . . . . ?
C13 C14 C16 C19 57.9(3) . . . . ?
Zr1 C14 C16 C19 168.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.15
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.060