#------------------------------------------------------------------------------
#$Date: 2015-09-06 03:09:49 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154729 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/61/4086113.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4086113
loop_
_publ_author_name
'Corbey, Jordan F.'
'Woen, David H.'
'Palumbo, Chad T.'
'Fieser, Megan E.'
'Ziller, Joseph W.'
'Furche, Filipp'
'Evans, William J.'
_publ_section_title
;
 Ligand Effects in the Synthesis of Ln2+Complexes by Reduction of
 Tris(cyclopentadienyl) Precursors Including C--H Bond Activation of an
 Indenyl Anion
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              3909
_journal_paper_doi               10.1021/acs.organomet.5b00500
_journal_volume                  34
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H29 O Y'
_chemical_formula_weight         506.45
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   11.6507(11)
_cell_length_b                   11.6507(11)
_cell_length_c                   10.0984(10)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.85
_cell_volume                     1187.1(2)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2013.10-0, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14058
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.623
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_T_max  0.8382
_exptl_absorpt_correction_T_min  0.4380
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2014/4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       rod
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.774
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
; 
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+1.1365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.861
_reflns_friedel_fraction_full    0.994
_reflns_friedel_fraction_max     0.935
_reflns_number_gt                1906
_reflns_number_total             1965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00500_si_003.cif
_cod_data_source_block           jfc50
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4086111--4086114.cif.
;
_cod_original_cell_volume        1187.1(3)
_cod_database_code               4086113
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.250
_shelx_estimated_absorpt_t_max   0.745
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Y1 Y 0.3333 0.6667 0.88005(9) 0.01343(16) Uani 1 3 d S T P A .
C1 C 0.0731(4) 0.5238(5) 0.9423(6) 0.0331(10) Uani 1 1 d . . . . .
H1A H 0.0379 0.4811 1.0302 0.040 Uiso 1 1 calc R U . . .
C2 C 0.0992(4) 0.4638(4) 0.8372(5) 0.0312(10) Uani 1 1 d . . . . .
H2A H 0.0793 0.3697 0.8381 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1245(4) 0.5392(4) 0.7225(5) 0.0292(9) Uani 1 1 d . . . . .
H3A H 0.1269 0.5078 0.6309 0.035 Uiso 1 1 calc R U . . .
C4 C 0.0973(4) 0.6458(4) 0.7547(5) 0.0274(9) Uani 1 1 d . . . . .
C5 C 0.0897(5) 0.7437(5) 0.6760(5) 0.0342(10) Uani 1 1 d . . . . .
H5A H 0.1134 0.7549 0.5850 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0473(5) 0.8202(6) 0.7363(7) 0.0451(13) Uani 1 1 d . . . . .
H6A H 0.0355 0.8815 0.6844 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0205(4) 0.8119(5) 0.8716(9) 0.0432(11) Uani 1 1 d . . . . .
H7A H -0.0078 0.8685 0.9089 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0337(5) 0.7253(6) 0.9519(6) 0.0422(12) Uani 1 1 d . . . . .
H8A H 0.0201 0.7247 1.0447 0.051 Uiso 1 1 calc R U . . .
C9 C 0.0681(4) 0.6367(4) 0.8935(7) 0.0310(10) Uani 1 1 d . . . . .
O1 O 0.3333 0.6667 1.1188(5) 0.0295(12) Uani 1 3 d DS T P . .
C10 C 0.337(2) 0.7677(15) 1.2046(12) 0.050(4) Uani 0.3333 1 d D U P A -1
H10A H 0.2909 0.8103 1.1625 0.060 Uiso 0.3333 1 calc R U P A -1
H10B H 0.4298 0.8367 1.2229 0.060 Uiso 0.3333 1 calc R U P A -1
C11 C 0.268(4) 0.700(2) 1.3309(19) 0.060(5) Uani 0.3333 1 d D U P A -1
H11A H 0.1706 0.6571 1.3231 0.072 Uiso 0.3333 1 calc R U P A -1
H11B H 0.2990 0.7616 1.4071 0.072 Uiso 0.3333 1 calc R U P A -1
C12 C 0.314(3) 0.599(3) 1.3399(13) 0.060(4) Uani 0.3333 1 d D U P A -1
H12A H 0.2527 0.5236 1.3962 0.072 Uiso 0.3333 1 calc R U P A -1
H12B H 0.4039 0.6403 1.3787 0.072 Uiso 0.3333 1 calc R U P A -1
C13 C 0.315(2) 0.5527(15) 1.1982(11) 0.041(3) Uani 0.3333 1 d D U P A -1
H13A H 0.3881 0.5345 1.1846 0.049 Uiso 0.3333 1 calc R U P A -1
H13B H 0.2296 0.4720 1.1766 0.049 Uiso 0.3333 1 calc R U P A -1
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'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Cnt Y1 Cnt 116.0 . .
Cnt Y1 O1 101.7 . .
O1 Y1 C2 99.56(12) . .
O1 Y1 C2 99.56(11) . 3_565
C2 Y1 C2 117.30(6) . 3_565
O1 Y1 C2 99.56(11) . 2_665
C2 Y1 C2 117.30(6) . 2_665
C2 Y1 C2 117.30(7) 3_565 2_665
O1 Y1 C3 126.84(11) . .
C2 Y1 C3 30.74(15) . .
C2 Y1 C3 95.49(15) 3_565 .
C2 Y1 C3 117.71(15) 2_665 .
O1 Y1 C3 126.84(11) . 3_565
C2 Y1 C3 117.71(15) . 3_565
C2 Y1 C3 30.74(15) 3_565 3_565
C2 Y1 C3 95.49(15) 2_665 3_565
C3 Y1 C3 87.75(16) . 3_565
O1 Y1 C3 126.84(11) . 2_665
C2 Y1 C3 95.49(15) . 2_665
C2 Y1 C3 117.71(15) 3_565 2_665
C2 Y1 C3 30.74(15) 2_665 2_665
C3 Y1 C3 87.75(16) . 2_665
C3 Y1 C3 87.75(16) 3_565 2_665
O1 Y1 C1 76.57(12) . 3_565
C2 Y1 C1 140.37(14) . 3_565
C2 Y1 C1 30.19(16) 3_565 3_565
C2 Y1 C1 102.12(14) 2_665 3_565
C3 Y1 C1 125.10(15) . 3_565
C3 Y1 C1 50.42(16) 3_565 3_565
C3 Y1 C1 118.70(14) 2_665 3_565
O1 Y1 C1 76.56(12) . .
C2 Y1 C1 30.19(16) . .
C2 Y1 C1 102.12(14) 3_565 .
C2 Y1 C1 140.37(14) 2_665 .
C3 Y1 C1 50.42(16) . .
C3 Y1 C1 118.70(14) 3_565 .
C3 Y1 C1 125.09(16) 2_665 .
C1 Y1 C1 114.77(9) 3_565 .
O1 Y1 C1 76.57(12) . 2_665
C2 Y1 C1 102.12(14) . 2_665
C2 Y1 C1 140.37(14) 3_565 2_665
C2 Y1 C1 30.19(16) 2_665 2_665
C3 Y1 C1 118.70(14) . 2_665
C3 Y1 C1 125.09(16) 3_565 2_665
C3 Y1 C1 50.42(16) 2_665 2_665
C1 Y1 C1 114.77(9) 3_565 2_665
C1 Y1 C1 114.77(9) . 2_665
O1 Y1 C4 115.65(10) . 2_665
C2 Y1 C4 69.39(14) . 2_665
C2 Y1 C4 143.01(15) 3_565 2_665
C2 Y1 C4 48.51(14) 2_665 2_665
C3 Y1 C4 72.94(13) . 2_665
C3 Y1 C4 112.43(14) 3_565 2_665
C3 Y1 C4 29.92(13) 2_665 2_665
C1 Y1 C4 148.15(13) 3_565 2_665
C1 Y1 C4 96.95(14) . 2_665
C1 Y1 C4 48.02(14) 2_665 2_665
O1 Y1 C4 115.65(10) . .
C2 Y1 C4 48.51(13) . .
C2 Y1 C4 69.39(14) 3_565 .
C2 Y1 C4 143.01(15) 2_665 .
C3 Y1 C4 29.92(13) . .
C3 Y1 C4 72.94(13) 3_565 .
C3 Y1 C4 112.43(15) 2_665 .
C1 Y1 C4 96.95(14) 3_565 .
C1 Y1 C4 48.02(14) . .
C1 Y1 C4 148.15(13) 2_665 .
C4 Y1 C4 102.65(12) 2_665 .
O1 Y1 C4 115.65(10) . 3_565
C2 Y1 C4 143.01(15) . 3_565
C2 Y1 C4 48.51(14) 3_565 3_565
C2 Y1 C4 69.39(14) 2_665 3_565
C3 Y1 C4 112.43(14) . 3_565
C3 Y1 C4 29.92(13) 3_565 3_565
C3 Y1 C4 72.94(13) 2_665 3_565
C1 Y1 C4 48.02(14) 3_565 3_565
C1 Y1 C4 148.15(13) . 3_565
C1 Y1 C4 96.95(14) 2_665 3_565
C4 Y1 C4 102.65(12) 2_665 3_565
C4 Y1 C4 102.65(12) . 3_565
O1 Y1 C9 87.35(13) . 3_565
C2 Y1 C9 165.38(14) . 3_565
C2 Y1 C9 48.42(14) 3_565 3_565
C2 Y1 C9 73.69(13) 2_665 3_565
C3 Y1 C9 136.84(16) . 3_565
C3 Y1 C9 49.09(16) 3_565 3_565
C3 Y1 C9 90.51(14) 2_665 3_565
C1 Y1 C9 29.08(13) 3_565 3_565
C1 Y1 C9 143.81(14) . 3_565
C1 Y1 C9 91.98(13) 2_665 3_565
C4 Y1 C9 119.23(13) 2_665 3_565
C4 Y1 C9 116.87(13) . 3_565
C4 Y1 C9 28.33(16) 3_565 3_565
O1 Y1 C9 87.35(13) . .
C2 Y1 C9 48.42(14) . .
C2 Y1 C9 73.69(13) 3_565 .
C2 Y1 C9 165.38(14) 2_665 .
C3 Y1 C9 49.08(16) . .
C3 Y1 C9 90.51(14) 3_565 .
C3 Y1 C9 136.83(16) 2_665 .
C1 Y1 C9 91.98(13) 3_565 .
C1 Y1 C9 29.08(13) . .
C1 Y1 C9 143.81(14) 2_665 .
C4 Y1 C9 116.87(13) 2_665 .
C4 Y1 C9 28.33(16) . .
C4 Y1 C9 119.23(13) 3_565 .
C9 Y1 C9 119.79(2) 3_565 .
O1 Y1 C9 87.35(13) . 2_665
C2 Y1 C9 73.69(13) . 2_665
C2 Y1 C9 165.38(14) 3_565 2_665
C2 Y1 C9 48.42(14) 2_665 2_665
C3 Y1 C9 90.51(14) . 2_665
C3 Y1 C9 136.84(16) 3_565 2_665
C3 Y1 C9 49.08(16) 2_665 2_665
C1 Y1 C9 143.81(14) 3_565 2_665
C1 Y1 C9 91.98(13) . 2_665
C1 Y1 C9 29.08(13) 2_665 2_665
C4 Y1 C9 28.33(16) 2_665 2_665
C4 Y1 C9 119.23(13) . 2_665
C4 Y1 C9 116.87(13) 3_565 2_665
C9 Y1 C9 119.79(2) 3_565 2_665
C9 Y1 C9 119.79(2) . 2_665
C2 C1 C9 108.7(5) . .
C2 C1 Y1 70.8(2) . .
C9 C1 Y1 84.4(3) . .
C1 C2 C3 110.4(4) . .
C1 C2 Y1 79.0(3) . .
C3 C2 Y1 76.7(2) . .
C2 C3 C4 106.4(4) . .
C2 C3 Y1 72.6(3) . .
C4 C3 Y1 85.3(2) . .
C5 C4 C9 119.7(4) . .
C5 C4 C3 132.8(5) . .
C9 C4 C3 107.4(4) . .
C5 C4 Y1 127.3(3) . .
C9 C4 Y1 76.2(2) . .
C3 C4 Y1 64.7(2) . .
C6 C5 C4 117.5(5) . .
C5 C6 C7 122.4(5) . .
C8 C7 C6 122.0(5) . .
C7 C8 C9 118.2(6) . .
C8 C9 C1 133.3(6) . .
C8 C9 C4 119.9(5) . .
C1 C9 C4 106.6(4) . .
C8 C9 Y1 126.9(3) . .
C1 C9 Y1 66.5(2) . .
C4 C9 Y1 75.4(2) . .
C10 O1 C13 109.8(8) . .
C10 O1 Y1 126.9(6) . .
C13 O1 Y1 123.0(5) . .
O1 C10 C11 106.9(12) . .
C10 C11 C12 99.0(16) . .
C11 C12 C13 106.5(12) . .
O1 C13 C12 102.4(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cnt Y1 2.489 .
Y1 O1 2.411(6) .
Y1 C2 2.602(4) .
Y1 C2 2.602(4) 3_565
Y1 C2 2.602(4) 2_665
Y1 C3 2.654(4) .
Y1 C3 2.654(4) 3_565
Y1 C3 2.654(4) 2_665
Y1 C1 2.704(4) 3_565
Y1 C1 2.704(4) .
Y1 C1 2.704(4) 2_665
Y1 C4 2.925(4) 2_665
Y1 C4 2.925(4) .
Y1 C4 2.925(4) 3_565
Y1 C9 2.935(4) 3_565
Y1 C9 2.935(4) .
Y1 C9 2.935(4) 2_665
C1 C2 1.385(7) .
C1 C9 1.433(6) .
C2 C3 1.394(7) .
C3 C4 1.464(6) .
C4 C5 1.428(6) .
C4 C9 1.434(8) .
C5 C6 1.360(8) .
C6 C7 1.394(11) .
C7 C8 1.361(9) .
C8 C9 1.409(7) .
O1 C10 1.446(11) .
O1 C13 1.471(10) .
C10 C11 1.502(13) .
C11 C12 1.514(13) .
C12 C13 1.532(13) .
