#------------------------------------------------------------------------------
#$Date: 2015-09-05 20:48:40 +0300 (Sat, 05 Sep 2015) $
#$Revision: 154504 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/62/4086235.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_4086235
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 Dy O'
_chemical_formula_weight         580.04
_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                   11.6494(11)
_cell_length_b                   11.6494(11)
_cell_length_c                   10.0857(9)
_cell_measurement_reflns_used    8796
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.86
_cell_volume                     1185.34(19)
_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 0.976
_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  0.0558
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.627
_diffrn_reflns_theta_min         2.019
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.173
_exptl_absorpt_correction_T_max  0.9385
_exptl_absorpt_correction_T_min  0.5377
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2014/4'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       rod
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.028
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
; 
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.067(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0224
_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)+(0.0272P)²+0.3662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0544
_reflns_Friedel_coverage         0.862
_reflns_friedel_fraction_full    0.999
_reflns_friedel_fraction_max     0.939
_reflns_number_gt                1796
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00500_si_005.cif
_cod_data_source_block           jfc55
_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 
;
_cod_original_cell_volume        1185.3(2)
_cod_database_code               4086235
_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   0.438
_shelx_estimated_absorpt_t_max   0.916
_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
Dy1 Dy 0.3333 0.6667 0.87757(14) 0.01328(10) Uani 1 3 d S T P A .
C1 C 0.1236(5) 0.5854(6) 1.0362(7) 0.0313(12) Uani 1 1 d . . . . .
H1 H 0.1519 0.6289 1.1194 0.038 Uiso 1 1 calc R U . . .
C2 C 0.0989(5) 0.6355(6) 0.9212(6) 0.0322(15) Uani 1 1 d . . . . .
H2 H 0.0999 0.7174 0.9159 0.039 Uiso 1 1 calc R U . . .
C3 C 0.0729(6) 0.5502(6) 0.8160(7) 0.0329(13) Uani 1 1 d . . . . .
H3 H 0.0607 0.5665 0.7263 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0674(5) 0.4304(5) 0.8674(14) 0.0351(16) Uani 1 1 d . . . . .
C5 C 0.0339(7) 0.3084(7) 0.8071(7) 0.0425(16) Uani 1 1 d . . . . .
H5 H 0.0212 0.2966 0.7140 0.051 Uiso 1 1 calc R U . . .
C6 C 0.0207(5) 0.2093(5) 0.8857(13) 0.0434(17) Uani 1 1 d . . . . .
H6 H -0.0072 0.1247 0.8479 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0467(7) 0.2272(7) 1.0215(9) 0.0486(18) Uani 1 1 d . . . . .
H7 H 0.0338 0.1538 1.0736 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0899(6) 0.3458(6) 1.0813(6) 0.0326(13) Uani 1 1 d . . . . .
H8 H 0.1144 0.3585 1.1722 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0971(5) 0.4512(5) 1.0027(6) 0.0268(12) Uani 1 1 d . . . . .
O1 O 0.3333 0.6667 0.6379(7) 0.0292(16) Uani 1 3 d DS T P . .
C10 C 0.2314(16) 0.660(3) 0.5516(15) 0.045(4) Uani 0.3333 1 d D U P A -1
H10A H 0.1862 0.7034 0.5938 0.054 Uiso 0.3333 1 calc R U P A -1
H10B H 0.1646 0.5665 0.5329 0.054 Uiso 0.3333 1 calc R U P A -1
C11 C 0.298(3) 0.731(4) 0.426(2) 0.061(6) Uani 0.3333 1 d D U P A -1
H11A H 0.3402 0.8281 0.4341 0.073 Uiso 0.3333 1 calc R U P A -1
H11B H 0.2370 0.6996 0.3490 0.073 Uiso 0.3333 1 calc R U P A -1
C12 C 0.400(4) 0.686(4) 0.4171(15) 0.059(5) Uani 0.3333 1 d D U P A -1
H12A H 0.4754 0.7474 0.3604 0.071 Uiso 0.3333 1 calc R U P A -1
H12B H 0.3597 0.5959 0.3785 0.071 Uiso 0.3333 1 calc R U P A -1
C13 C 0.4480(16) 0.686(3) 0.5588(14) 0.038(4) Uani 0.3333 1 d D U P A -1
H13A H 0.4667 0.6129 0.5724 0.046 Uiso 0.3333 1 calc R U P A -1
H13B H 0.5283 0.7715 0.5802 0.046 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'
Dy Dy -0.1892 4.4098 '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 Dy1 Cnt1 115.8 . .
Cnt Dy1 O1 101.9 . .
O1 Dy1 C2 99.73(15) . .
O1 Dy1 C2 99.73(15) . 3_565
C2 Dy1 C2 117.20(8) . 3_565
O1 Dy1 C2 99.73(14) . 2_665
C2 Dy1 C2 117.20(8) . 2_665
C2 Dy1 C2 117.20(8) 3_565 2_665
O1 Dy1 C1 126.86(15) . .
C2 Dy1 C1 30.6(2) . .
C2 Dy1 C1 117.5(2) 3_565 .
C2 Dy1 C1 95.46(19) 2_665 .
O1 Dy1 C1 126.86(15) . 3_565
C2 Dy1 C1 95.46(19) . 3_565
C2 Dy1 C1 30.6(2) 3_565 3_565
C2 Dy1 C1 117.5(2) 2_665 3_565
C1 Dy1 C1 87.7(2) . 3_565
O1 Dy1 C1 126.86(15) . 2_665
C2 Dy1 C1 117.5(2) . 2_665
C2 Dy1 C1 95.46(19) 3_565 2_665
C2 Dy1 C1 30.6(2) 2_665 2_665
C1 Dy1 C1 87.7(2) . 2_665
C1 Dy1 C1 87.7(2) 3_565 2_665
O1 Dy1 C3 76.73(15) . .
C2 Dy1 C3 30.05(19) . .
C2 Dy1 C3 140.18(17) 3_565 .
C2 Dy1 C3 102.35(17) 2_665 .
C1 Dy1 C3 50.3(2) . .
C1 Dy1 C3 124.9(2) 3_565 .
C1 Dy1 C3 118.69(18) 2_665 .
O1 Dy1 C3 76.73(15) . 3_565
C2 Dy1 C3 102.35(17) . 3_565
C2 Dy1 C3 30.05(19) 3_565 3_565
C2 Dy1 C3 140.18(17) 2_665 3_565
C1 Dy1 C3 118.69(18) . 3_565
C1 Dy1 C3 50.3(2) 3_565 3_565
C1 Dy1 C3 124.9(2) 2_665 3_565
C3 Dy1 C3 114.90(11) . 3_565
O1 Dy1 C3 76.73(15) . 2_665
C2 Dy1 C3 140.18(17) . 2_665
C2 Dy1 C3 102.35(17) 3_565 2_665
C2 Dy1 C3 30.05(19) 2_665 2_665
C1 Dy1 C3 124.9(2) . 2_665
C1 Dy1 C3 118.69(18) 3_565 2_665
C1 Dy1 C3 50.3(2) 2_665 2_665
C3 Dy1 C3 114.90(11) . 2_665
C3 Dy1 C3 114.90(11) 3_565 2_665
O1 Dy1 C9 115.56(12) . 3_565
C2 Dy1 C9 69.28(18) . 3_565
C2 Dy1 C9 48.46(18) 3_565 3_565
C2 Dy1 C9 142.95(19) 2_665 3_565
C1 Dy1 C9 72.86(17) . 3_565
C1 Dy1 C9 30.09(17) 3_565 3_565
C1 Dy1 C9 112.54(19) 2_665 3_565
C3 Dy1 C9 96.63(18) . 3_565
C3 Dy1 C9 47.97(18) 3_565 3_565
C3 Dy1 C9 148.33(17) 2_665 3_565
O1 Dy1 C9 115.56(13) . .
C2 Dy1 C9 48.46(18) . .
C2 Dy1 C9 142.95(19) 3_565 .
C2 Dy1 C9 69.28(19) 2_665 .
C1 Dy1 C9 30.09(17) . .
C1 Dy1 C9 112.54(19) 3_565 .
C1 Dy1 C9 72.86(18) 2_665 .
C3 Dy1 C9 47.97(18) . .
C3 Dy1 C9 148.33(17) 3_565 .
C3 Dy1 C9 96.63(18) 2_665 .
C9 Dy1 C9 102.76(15) 3_565 .
O1 Dy1 C9 115.56(12) . 2_665
C2 Dy1 C9 142.95(19) . 2_665
C2 Dy1 C9 69.28(18) 3_565 2_665
C2 Dy1 C9 48.46(18) 2_665 2_665
C1 Dy1 C9 112.55(19) . 2_665
C1 Dy1 C9 72.86(17) 3_565 2_665
C1 Dy1 C9 30.10(17) 2_665 2_665
C3 Dy1 C9 148.33(17) . 2_665
C3 Dy1 C9 96.63(18) 3_565 2_665
C3 Dy1 C9 47.97(18) 2_665 2_665
C9 Dy1 C9 102.76(15) 3_565 2_665
C9 Dy1 C9 102.76(15) . 2_665
O1 Dy1 C4 88.0(3) . 3_565
C2 Dy1 C4 73.49(18) . 3_565
C2 Dy1 C4 48.37(18) 3_565 3_565
C2 Dy1 C4 165.1(2) 2_665 3_565
C1 Dy1 C4 89.9(2) . 3_565
C1 Dy1 C4 48.7(3) 3_565 3_565
C1 Dy1 C4 136.4(3) 2_665 3_565
C3 Dy1 C4 91.83(17) . 3_565
C3 Dy1 C4 29.58(19) 3_565 3_565
C3 Dy1 C4 144.5(2) 2_665 3_565
C9 Dy1 C4 27.6(3) 3_565 3_565
C9 Dy1 C4 118.90(19) . 3_565
C9 Dy1 C4 116.6(2) 2_665 3_565
O1 Dy1 C4 88.0(3) . .
C2 Dy1 C4 48.37(18) . .
C2 Dy1 C4 165.1(2) 3_565 .
C2 Dy1 C4 73.49(18) 2_665 .
C1 Dy1 C4 48.7(3) . .
C1 Dy1 C4 136.4(3) 3_565 .
C1 Dy1 C4 89.9(2) 2_665 .
C3 Dy1 C4 29.58(19) . .
C3 Dy1 C4 144.5(2) 3_565 .
C3 Dy1 C4 91.83(18) 2_665 .
C9 Dy1 C4 116.6(2) 3_565 .
C9 Dy1 C4 27.6(3) . .
C9 Dy1 C4 118.9(2) 2_665 .
C4 Dy1 C4 119.88(4) 3_565 .
O1 Dy1 C4 88.0(3) . 2_665
C2 Dy1 C4 165.1(2) . 2_665
C2 Dy1 C4 73.49(18) 3_565 2_665
C2 Dy1 C4 48.37(18) 2_665 2_665
C1 Dy1 C4 136.4(3) . 2_665
C1 Dy1 C4 90.0(2) 3_565 2_665
C1 Dy1 C4 48.7(3) 2_665 2_665
C3 Dy1 C4 144.5(2) . 2_665
C3 Dy1 C4 91.83(18) 3_565 2_665
C3 Dy1 C4 29.58(19) 2_665 2_665
C9 Dy1 C4 118.9(2) 3_565 2_665
C9 Dy1 C4 116.6(2) . 2_665
C9 Dy1 C4 27.6(3) 2_665 2_665
C4 Dy1 C4 119.88(4) 3_565 2_665
C4 Dy1 C4 119.88(3) . 2_665
C2 C1 C9 106.1(6) . .
C2 C1 Dy1 72.3(3) . .
C9 C1 Dy1 84.8(3) . .
C3 C2 C1 110.8(5) . .
C3 C2 Dy1 78.9(3) . .
C1 C2 Dy1 77.1(3) . .
C2 C3 C4 107.7(7) . .
C2 C3 Dy1 71.0(3) . .
C4 C3 Dy1 84.3(3) . .
C9 C4 C5 121.0(7) . .
C9 C4 C3 107.0(6) . .
C5 C4 C3 131.9(10) . .
C9 C4 Dy1 75.6(3) . .
C5 C4 Dy1 126.1(5) . .
C3 C4 Dy1 66.1(3) . .
C6 C5 C4 117.8(7) . .
C5 C6 C7 121.8(7) . .
C8 C7 C6 122.2(6) . .
C7 C8 C9 117.5(6) . .
C4 C9 C8 119.3(5) . .
C4 C9 C1 108.0(5) . .
C8 C9 C1 132.6(6) . .
C4 C9 Dy1 76.9(3) . .
C8 C9 Dy1 127.1(4) . .
C1 C9 Dy1 65.2(3) . .
C10 O1 C13 109.9(10) . .
C10 O1 Dy1 127.1(7) . .
C13 O1 Dy1 122.8(7) . .
O1 C10 C11 107.0(13) . .
C10 C11 C12 98.1(17) . .
C11 C12 C13 107.1(13) . .
O1 C13 C12 101.7(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cnt Dy1 2.496 .
Dy1 O1 2.417(7) .
Dy1 C2 2.606(5) .
Dy1 C2 2.606(5) 3_565
Dy1 C2 2.606(5) 2_665
Dy1 C1 2.667(6) .
Dy1 C1 2.667(6) 3_565
Dy1 C1 2.667(6) 2_665
Dy1 C3 2.705(6) .
Dy1 C3 2.705(6) 3_565
Dy1 C3 2.705(6) 2_665
Dy1 C9 2.926(6) 3_565
Dy1 C9 2.926(6) .
Dy1 C9 2.926(6) 2_665
Dy1 C4 2.942(5) 3_565
Dy1 C4 2.942(5) .
Dy1 C4 2.942(5) 2_665
C1 C2 1.391(9) .
C1 C9 1.473(8) .
C2 C3 1.380(9) .
C3 C4 1.460(9) .
C4 C9 1.399(14) .
C4 C5 1.410(10) .
C5 C6 1.345(12) .
C6 C7 1.395(15) .
C7 C8 1.353(10) .
C8 C9 1.428(8) .
O1 C10 1.443(12) .
O1 C13 1.473(11) .
C10 C11 1.503(13) .
C11 C12 1.516(14) .
C12 C13 1.534(13) .
