#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:24:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179244 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/64/4316471.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_4316471
loop_
_publ_author_name
'Chengfu Pi'
'Xiaoqing Li'
'Lili Zhang'
'Ruiting Liu'
'Linhong Weng'
'Xigeng Zhou'
_publ_section_title
;
 A New Strategy for Ring Modification of Metallocenes: Carbodiimide
 Insertion into the η5-Y-C5H5 Bond and Subsequent Isomerization
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7632
_journal_page_last               7634
_journal_paper_doi               10.1021/ic101346b
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C22 H29 N2 Y'
_chemical_formula_weight         410.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.301(15)
_cell_angle_beta                 102.283(15)
_cell_angle_gamma                107.941(14)
_cell_formula_units_Z            2
_cell_length_a                   8.392(9)
_cell_length_b                   10.643(12)
_cell_length_c                   12.394(14)
_cell_measurement_reflns_used    766
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.143
_cell_measurement_theta_min      2.487
_cell_volume                     1022(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_sigmaI/netI    0.1084
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4287
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        9.33
_exptl_absorpt_coefficient_mu    2.858
_exptl_absorpt_correction_T_max  0.5987
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1171P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1894
_reflns_number_gt                2417
_reflns_number_total             3549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101346b_si_002_1.cif
_cod_data_source_block           f61021a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4316471
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Y1 Y 0.05271(8) 0.25115(7) 0.80888(6) 0.0375(3) Uani 1 1 d . . .
N1 N 0.0745(7) 0.0295(5) 0.7403(5) 0.0371(13) Uani 1 1 d . . .
N2 N -0.1866(8) -0.1510(6) 0.6470(5) 0.0452(15) Uani 1 1 d . . .
C1 C -0.2594(10) 0.1877(9) 0.8702(7) 0.059(2) Uani 1 1 d . . .
H1A H -0.2746 0.1808 0.9462 0.070 Uiso 1 1 calc R . .
C2 C -0.2697(9) 0.0831(8) 0.7953(7) 0.051(2) Uani 1 1 d . . .
H2A H -0.2986 -0.0105 0.8089 0.062 Uiso 1 1 calc R . .
C3 C -0.2743(9) 0.1290(9) 0.6916(7) 0.054(2) Uani 1 1 d . . .
H3A H -0.3073 0.0725 0.6209 0.065 Uiso 1 1 calc R . .
C4 C -0.2633(9) 0.2622(9) 0.7027(7) 0.057(2) Uani 1 1 d . . .
H4A H -0.2846 0.3145 0.6412 0.068 Uiso 1 1 calc R . .
C5 C -0.2480(10) 0.3004(10) 0.8129(8) 0.066(3) Uani 1 1 d . . .
H5A H -0.2562 0.3845 0.8422 0.079 Uiso 1 1 calc R . .
C6 C 0.0662(16) 0.3811(19) 0.6234(12) 0.111(5) Uani 1 1 d . . .
H6A H -0.0343 0.3813 0.5663 0.134 Uiso 1 1 calc R . .
C7 C 0.148(2) 0.4753(11) 0.7117(15) 0.105(5) Uani 1 1 d . . .
H7A H 0.1186 0.5556 0.7264 0.126 Uiso 1 1 calc R . .
C8 C 0.3043(15) 0.4541(12) 0.7622(8) 0.093(4) Uani 1 1 d . . .
H8A H 0.4037 0.5167 0.8153 0.111 Uiso 1 1 calc R . .
C9 C 0.3014(13) 0.3413(10) 0.6979(9) 0.070(3) Uani 1 1 d . . .
H9A H 0.3995 0.3091 0.7000 0.085 Uiso 1 1 calc R . .
C10 C 0.1533(17) 0.3030(13) 0.6183(8) 0.087(3) Uani 1 1 d . . .
H10A H 0.1278 0.2352 0.5556 0.104 Uiso 1 1 calc R . .
C11 C 0.1124(11) 0.3202(9) 1.0299(6) 0.062(2) Uani 1 1 d . . .
H11A H 0.0450 0.3611 1.0665 0.075 Uiso 1 1 calc R . .
C12 C 0.2658(12) 0.3871(8) 1.0007(7) 0.067(3) Uani 1 1 d . . .
H12A H 0.3231 0.4835 1.0131 0.080 Uiso 1 1 calc R . .
C13 C 0.3410(11) 0.2944(10) 0.9757(7) 0.065(2) Uani 1 1 d . . .
H13A H 0.4587 0.3153 0.9656 0.078 Uiso 1 1 calc R . .
C14 C 0.2399(11) 0.1731(9) 0.9895(6) 0.059(2) Uani 1 1 d . . .
H14A H 0.2722 0.0921 0.9883 0.070 Uiso 1 1 calc R . .
C15 C 0.0986(11) 0.1844(9) 1.0226(6) 0.056(2) Uani 1 1 d . . .
H15A H 0.0162 0.1143 1.0505 0.067 Uiso 1 1 calc R . .
C16 C 0.2422(9) 0.0052(7) 0.7360(6) 0.0442(17) Uani 1 1 d . . .
H16A H 0.3373 0.0852 0.7719 0.053 Uiso 1 1 calc R . .
C17 C 0.2515(12) -0.0152(9) 0.6171(7) 0.068(3) Uani 1 1 d . . .
H17A H 0.2365 0.0593 0.5800 0.102 Uiso 1 1 calc R . .
H17B H 0.1621 -0.0950 0.5806 0.102 Uiso 1 1 calc R . .
H17C H 0.3618 -0.0228 0.6148 0.102 Uiso 1 1 calc R . .
C18 C 0.2635(12) -0.1078(9) 0.7974(8) 0.070(3) Uani 1 1 d . . .
H18A H 0.2577 -0.0912 0.8729 0.105 Uiso 1 1 calc R . .
H18B H 0.3733 -0.1173 0.7963 0.105 Uiso 1 1 calc R . .
H18C H 0.1732 -0.1881 0.7627 0.105 Uiso 1 1 calc R . .
C19 C -0.0587(9) -0.0656(7) 0.6985(6) 0.0380(16) Uani 1 1 d . . .
C20 C -0.3141(9) -0.2683(7) 0.6722(6) 0.0480(18) Uani 1 1 d . . .
H20A H -0.3250 -0.2534 0.7484 0.058 Uiso 1 1 calc R . .
C21 C -0.4846(10) -0.2840(9) 0.5915(8) 0.072(3) Uani 1 1 d . . .
H21A H -0.5165 -0.2059 0.6017 0.108 Uiso 1 1 calc R . .
H21B H -0.5721 -0.3601 0.6052 0.108 Uiso 1 1 calc R . .
H21C H -0.4731 -0.2959 0.5167 0.108 Uiso 1 1 calc R . .
C22 C -0.2588(12) -0.3859(8) 0.6605(8) 0.067(2) Uani 1 1 d . . .
H22A H -0.1511 -0.3725 0.7129 0.100 Uiso 1 1 calc R . .
H22B H -0.2447 -0.3989 0.5865 0.100 Uiso 1 1 calc R . .
H22C H -0.3445 -0.4629 0.6747 0.100 Uiso 1 1 calc R . .
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
N1 Y1 C7 124.2(3) . . ?
N1 Y1 C10 77.5(3) . . ?
C7 Y1 C10 47.0(4) . . ?
N1 Y1 C9 80.9(3) . . ?
C7 Y1 C9 48.7(3) . . ?
C10 Y1 C9 29.0(3) . . ?
N1 Y1 C12 119.5(3) . . ?
C7 Y1 C12 88.1(5) . . ?
C10 Y1 C12 118.2(3) . . ?
C9 Y1 C12 91.2(3) . . ?
N1 Y1 C8 110.3(4) . . ?
C7 Y1 C8 30.5(4) . . ?
C10 Y1 C8 48.6(3) . . ?
C9 Y1 C8 30.2(3) . . ?
C12 Y1 C8 70.9(3) . . ?
N1 Y1 C3 79.5(2) . . ?
C7 Y1 C3 102.6(5) . . ?
C10 Y1 C3 90.1(3) . . ?
C9 Y1 C3 118.8(3) . . ?
C12 Y1 C3 147.8(3) . . ?
C8 Y1 C3 130.0(3) . . ?
N1 Y1 C11 119.3(2) . . ?
C7 Y1 C11 108.1(4) . . ?
C10 Y1 C11 147.5(3) . . ?
C9 Y1 C11 121.2(3) . . ?
C12 Y1 C11 30.0(3) . . ?
C8 Y1 C11 99.0(3) . . ?
C3 Y1 C11 119.1(3) . . ?
N1 Y1 C2 77.9(2) . . ?
C7 Y1 C2 128.4(5) . . ?
C10 Y1 C2 118.1(3) . . ?
C9 Y1 C2 145.1(3) . . ?
C12 Y1 C2 123.4(3) . . ?
C8 Y1 C2 158.5(4) . . ?
C3 Y1 C2 29.8(3) . . ?
C11 Y1 C2 93.5(3) . . ?
N1 Y1 C13 90.8(2) . . ?
C7 Y1 C13 99.9(5) . . ?
C10 Y1 C13 108.0(4) . . ?
C9 Y1 C13 79.3(3) . . ?
C12 Y1 C13 29.5(3) . . ?
C8 Y1 C13 72.6(3) . . ?
C3 Y1 C13 157.3(3) . . ?
C11 Y1 C13 48.9(3) . . ?
C2 Y1 C13 128.2(3) . . ?
N1 Y1 C6 101.1(5) . . ?
C7 Y1 C6 29.0(4) . . ?
C10 Y1 C6 27.1(4) . . ?
C9 Y1 C6 47.1(3) . . ?
C12 Y1 C6 116.2(4) . . ?
C8 Y1 C6 48.8(4) . . ?
C3 Y1 C6 81.4(4) . . ?
C11 Y1 C6 136.5(5) . . ?
C2 Y1 C6 111.0(3) . . ?
C13 Y1 C6 120.9(4) . . ?
N1 Y1 C4 107.8(2) . . ?
C7 Y1 C4 79.5(4) . . ?
C10 Y1 C4 87.7(4) . . ?
C9 Y1 C4 114.3(3) . . ?
C12 Y1 C4 129.3(3) . . ?
C8 Y1 C4 109.9(4) . . ?
C3 Y1 C4 29.6(2) . . ?
C11 Y1 C4 110.2(3) . . ?
C2 Y1 C4 48.9(3) . . ?
C13 Y1 C4 158.1(3) . . ?
C6 Y1 C4 67.8(3) . . ?
C19 N1 C16 114.9(5) . . ?
C19 N1 Y1 120.3(4) . . ?
C16 N1 Y1 124.6(4) . . ?
C19 N2 C20 136.5(7) . . ?
C2 C1 C5 107.9(8) . . ?
C2 C1 Y1 72.9(4) . . ?
C5 C1 Y1 73.9(5) . . ?
C1 C2 C3 107.5(8) . . ?
C1 C2 Y1 77.8(4) . . ?
C3 C2 Y1 74.6(4) . . ?
C2 C3 C4 108.5(7) . . ?
C2 C3 Y1 75.6(4) . . ?
C4 C3 Y1 76.7(4) . . ?
C5 C4 C3 108.1(8) . . ?
C5 C4 Y1 75.5(5) . . ?
C3 C4 Y1 73.6(4) . . ?
C4 C5 C1 107.9(8) . . ?
C4 C5 Y1 75.4(4) . . ?
C1 C5 Y1 76.5(5) . . ?
C10 C6 C7 109.4(12) . . ?
C10 C6 Y1 74.7(7) . . ?
C7 C6 Y1 73.8(7) . . ?
C6 C7 C8 107.8(10) . . ?
C6 C7 Y1 77.3(7) . . ?
C8 C7 Y1 74.9(6) . . ?
C9 C8 C7 103.7(9) . . ?
C9 C8 Y1 74.8(5) . . ?
C7 C8 Y1 74.6(6) . . ?
C10 C9 C8 107.4(10) . . ?
C10 C9 Y1 75.5(6) . . ?
C8 C9 Y1 74.9(5) . . ?
C6 C10 C9 111.6(12) . . ?
C6 C10 Y1 78.2(7) . . ?
C9 C10 Y1 75.5(6) . . ?
C12 C11 C15 106.2(8) . . ?
C12 C11 Y1 74.6(5) . . ?
C15 C11 Y1 76.7(4) . . ?
C13 C12 C11 108.2(8) . . ?
C13 C12 Y1 76.6(5) . . ?
C11 C12 Y1 75.4(4) . . ?
C14 C13 C12 108.5(9) . . ?
C14 C13 Y1 77.1(5) . . ?
C12 C13 Y1 73.9(5) . . ?
C13 C14 C15 109.5(8) . . ?
C13 C14 Y1 74.5(5) . . ?
C15 C14 Y1 75.1(5) . . ?
C14 C15 C11 107.6(8) . . ?
C14 C15 Y1 76.1(5) . . ?
C11 C15 Y1 73.4(5) . . ?
C18 C16 C17 111.8(7) . . ?
C18 C16 N1 111.8(6) . . ?
C17 C16 N1 109.8(6) . . ?
N2 C19 N1 172.6(7) . . ?
N2 C20 C22 109.8(7) . . ?
N2 C20 C21 106.8(6) . . ?
C22 C20 C21 111.9(7) . . ?
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
Y1 N1 2.547(6) . ?
Y1 C7 2.691(11) . ?
Y1 C10 2.694(10) . ?
Y1 C9 2.695(9) . ?
Y1 C12 2.695(8) . ?
Y1 C8 2.696(9) . ?
Y1 C3 2.699(8) . ?
Y1 C11 2.706(8) . ?
Y1 C2 2.711(8) . ?
Y1 C13 2.729(8) . ?
Y1 C6 2.735(11) . ?
Y1 C4 2.739(8) . ?
N1 C19 1.248(8) . ?
N1 C16 1.519(9) . ?
N2 C19 1.203(8) . ?
N2 C20 1.466(9) . ?
C1 C2 1.390(11) . ?
C1 C5 1.407(13) . ?
C2 C3 1.390(12) . ?
C3 C4 1.391(12) . ?
C4 C5 1.376(12) . ?
C6 C10 1.272(17) . ?
C6 C7 1.357(18) . ?
C7 C8 1.417(18) . ?
C8 C9 1.405(15) . ?
C9 C10 1.348(15) . ?
C11 C12 1.396(13) . ?
C11 C15 1.411(12) . ?
C12 C13 1.382(13) . ?
C13 C14 1.349(12) . ?
C14 C15 1.372(12) . ?
C16 C18 1.486(12) . ?
C16 C17 1.502(11) . ?
C20 C22 1.475(11) . ?
C20 C21 1.518(11) . ?
