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#$Date: 2016-10-05 12:46:34 +0300 (Wed, 05 Oct 2016) $
#$Revision: 186962 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/66/4086661.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_4086661
loop_
_publ_author_name
'Garner, Mary E.'
'Hohloch, Stephan'
'Maron, Laurent'
'Arnold, John'
_publ_section_title
;
 A New Supporting Ligand in Actinide Chemistry Leads to Reactive
 Bis(NHC)borate-Supported Thorium Complexes
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              2915
_journal_paper_doi               10.1021/acs.organomet.6b00467
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C48 H56 B2 Li2 N8'
_chemical_formula_weight         780.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.4510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7934(7)
_cell_length_b                   9.9360(3)
_cell_length_c                   19.8180(6)
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.07
_cell_volume                     4645.6(2)
_computing_cell_refinement       'Bruker Apex II suite, 2015'
_computing_data_collection       'Bruker Apex II suite, 2015'
_computing_data_reduction        'Bruker Apex II suite, 2015'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Quazar'
_diffrn_measurement_method       'omega phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26165
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.073
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1015P)²+1.9319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3751
_reflns_number_total             4753
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00467_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4086660--4086666.cif.'
_cod_database_code               4086661
_shelx_shelxl_version_number     2014/7
_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   0.993
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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'
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
N3 N 0.52510(5) 0.67014(13) 0.62152(6) 0.0183(3) Uani 1 1 d . .
N1 N 0.34561(5) 0.65623(13) 0.58168(6) 0.0199(3) Uani 1 1 d . .
N4 N 0.56310(5) 0.47810(13) 0.64842(6) 0.0193(3) Uani 1 1 d . .
N2 N 0.42587(5) 0.75822(13) 0.59350(6) 0.0193(3) Uani 1 1 d . .
C1 C 0.39534(6) 0.66750(16) 0.62493(8) 0.0201(3) Uani 1 1 d . .
C13 C 0.29722(6) 0.57515(16) 0.59243(7) 0.0200(3) Uani 1 1 d . .
C22 C 0.58320(6) 0.36136(16) 0.68733(8) 0.0199(3) Uani 1 1 d . .
C27 C 0.63467(6) 0.37026(16) 0.73001(8) 0.0215(3) Uani 1 1 d . .
C18 C 0.25156(6) 0.63799(16) 0.61745(8) 0.0215(4) Uani 1 1 d . .
C8 C 0.56643(6) 0.49568(17) 0.57984(7) 0.0219(4) Uani 1 1 d . .
H8 H 0.5824 0.4355 0.5503 0.026 Uiso 1 1 calc R U
C7 C 0.54231(6) 0.61569(17) 0.56363(8) 0.0218(3) Uani 1 1 d . .
H7 H 0.5379 0.6560 0.5198 0.026 Uiso 1 1 calc R U
C17 C 0.20408(6) 0.56023(17) 0.62553(8) 0.0235(4) Uani 1 1 d . .
H17 H 0.1726 0.6016 0.6422 0.028 Uiso 1 1 calc R U
C2 C 0.53768(6) 0.58546(16) 0.67518(7) 0.0186(3) Uani 1 1 d . .
C23 C 0.55065(6) 0.24418(17) 0.68146(8) 0.0239(4) Uani 1 1 d . .
C6 C 0.39618(6) 0.80254(16) 0.53325(8) 0.0221(3) Uani 1 1 d . .
H6 H 0.4090 0.8661 0.5028 0.027 Uiso 1 1 calc R U
C14 C 0.29627(6) 0.43895(17) 0.57627(8) 0.0217(3) Uani 1 1 d . .
C16 C 0.20152(6) 0.42421(18) 0.60991(8) 0.0255(4) Uani 1 1 d . .
C5 C 0.34567(6) 0.73905(17) 0.52542(8) 0.0239(4) Uani 1 1 d . .
H5 H 0.3161 0.7491 0.4887 0.029 Uiso 1 1 calc R U
C30 C 0.67057(6) 0.49530(17) 0.73302(9) 0.0253(4) Uani 1 1 d . .
H30A H 0.6528 0.5661 0.7574 0.038 Uiso 1 1 calc R U
H30B H 0.6739 0.5258 0.6867 0.038 Uiso 1 1 calc R U
H30C H 0.7083 0.4755 0.7569 0.038 Uiso 1 1 calc R U
C15 C 0.24763(6) 0.36519(17) 0.58535(8) 0.0246(4) Uani 1 1 d . .
H15 H 0.2462 0.2721 0.5744 0.030 Uiso 1 1 calc R U
C26 C 0.65209(7) 0.25759(17) 0.76898(8) 0.0267(4) Uani 1 1 d . .
H26 H 0.6867 0.2611 0.7987 0.032 Uiso 1 1 calc R U
C24 C 0.57041(7) 0.13447(17) 0.72104(9) 0.0278(4) Uani 1 1 d . .
H24 H 0.5491 0.0533 0.7174 0.033 Uiso 1 1 calc R U
C21 C 0.25359(7) 0.78325(18) 0.63745(9) 0.0288(4) Uani 1 1 d . .
H21A H 0.2151 0.8155 0.6405 0.043 Uiso 1 1 calc R U
H21B H 0.2703 0.8359 0.6032 0.043 Uiso 1 1 calc R U
H21C H 0.2768 0.7936 0.6818 0.043 Uiso 1 1 calc R U
C25 C 0.62016(7) 0.14008(18) 0.76553(9) 0.0295(4) Uani 1 1 d . .
C19 C 0.34577(7) 0.37142(19) 0.54992(9) 0.0307(4) Uani 1 1 d . .
H19A H 0.3514 0.4109 0.5060 0.046 Uiso 1 1 calc R U
H19B H 0.3381 0.2749 0.5441 0.046 Uiso 1 1 calc R U
H19C H 0.3800 0.3844 0.5825 0.046 Uiso 1 1 calc R U
C28 C 0.49571(7) 0.23618(19) 0.63468(9) 0.0327(4) Uani 1 1 d . .
H28A H 0.4788 0.1470 0.6385 0.049 Uiso 1 1 calc R U
H28B H 0.5029 0.2510 0.5877 0.049 Uiso 1 1 calc R U
H28C H 0.4696 0.3053 0.6474 0.049 Uiso 1 1 calc R U
C20 C 0.14945(7) 0.3432(2) 0.61949(11) 0.0386(5) Uani 1 1 d . .
H20A H 0.1429 0.3476 0.6673 0.058 Uiso 1 1 calc R U
H20B H 0.1551 0.2493 0.6068 0.058 Uiso 1 1 calc R U
H20C H 0.1165 0.3802 0.5906 0.058 Uiso 1 1 calc R U
B1 B 0.48764(7) 0.79851(18) 0.62330(9) 0.0208(4) Uani 1 1 d . .
H1A H 0.5017 0.8710 0.5956 0.025 Uiso 1 1 calc R U
H1B H 0.4886 0.8312 0.6706 0.025 Uiso 1 1 calc R U
C29 C 0.64034(9) 0.0200(2) 0.80877(12) 0.0454(5) Uani 1 1 d . .
H29A H 0.6312 -0.0628 0.7828 0.068 Uiso 1 1 calc R U
H29B H 0.6214 0.0190 0.8499 0.068 Uiso 1 1 calc R U
H29C H 0.6814 0.0260 0.8217 0.068 Uiso 1 1 calc R U
Li1 Li 0.45027(10) 0.6148(3) 0.71482(13) 0.0260(6) Uani 1 1 d . .
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'
B B 0.0013 0.0007 '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'
Li Li -0.0003 0.0001 '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
C2 N3 C7 110.45(13) . .
C2 N3 B1 123.88(12) . .
C7 N3 B1 124.93(12) . .
C1 N1 C5 111.30(12) . .
C1 N1 C13 126.36(12) . .
C5 N1 C13 122.28(12) . .
C2 N4 C8 111.55(13) . .
C2 N4 C22 123.65(12) . .
C8 N4 C22 124.80(13) . .
C1 N2 C6 111.40(12) . .
C1 N2 B1 121.95(12) . .
C6 N2 B1 126.61(13) . .
N2 C1 N1 103.69(13) . .
N2 C1 Li1 103.86(12) . .
N1 C1 Li1 152.44(14) . .
C14 C13 C18 121.74(14) . .
C14 C13 N1 119.92(13) . .
C18 C13 N1 118.31(14) . .
C23 C22 C27 122.45(14) . .
C23 C22 N4 119.05(13) . .
C27 C22 N4 118.50(13) . .
C26 C27 C22 117.33(15) . .
C26 C27 C30 121.03(14) . .
C22 C27 C30 121.63(14) . .
C17 C18 C13 118.12(15) . .
C17 C18 C21 120.18(14) . .
C13 C18 C21 121.66(14) . .
C7 C8 N4 105.65(13) . .
C7 C8 H8 127.2 . .
N4 C8 H8 127.2 . .
C8 C7 N3 108.26(13) . .
C8 C7 H7 125.9 . .
N3 C7 H7 125.9 . .
C16 C17 C18 121.82(14) . .
C16 C17 H17 119.1 . .
C18 C17 H17 119.1 . .
N3 C2 N4 104.09(12) . .
N3 C2 Li1 133.36(14) . 2_656
N4 C2 Li1 118.99(12) . 2_656
N3 C2 Li1 94.05(11) . .
N4 C2 Li1 133.33(13) . .
Li1 C2 Li1 69.78(11) 2_656 .
C24 C23 C22 117.68(15) . .
C24 C23 C28 120.68(15) . .
C22 C23 C28 121.64(15) . .
C5 C6 N2 107.41(14) . .
C5 C6 H6 126.3 . .
N2 C6 H6 126.3 . .
C13 C14 C15 117.96(14) . .
C13 C14 C19 121.55(14) . .
C15 C14 C19 120.49(15) . .
C17 C16 C15 118.48(14) . .
C17 C16 C20 120.30(15) . .
C15 C16 C20 121.22(16) . .
C6 C5 N1 106.20(13) . .
C6 C5 H5 126.9 . .
N1 C5 H5 126.9 . .
C27 C30 H30A 109.5 . .
C27 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C27 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C16 C15 C14 121.88(16) . .
C16 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
C25 C26 C27 121.79(15) . .
C25 C26 H26 119.1 . .
C27 C26 H26 119.1 . .
C25 C24 C23 121.85(16) . .
C25 C24 H24 119.1 . .
C23 C24 H24 119.1 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C24 C25 C26 118.85(15) . .
C24 C25 C29 120.87(17) . .
C26 C25 C29 120.27(16) . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C23 C28 H28A 109.5 . .
C23 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C23 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C16 C20 H20A 109.5 . .
C16 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C16 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N3 B1 N2 107.11(12) . .
N3 B1 Li1 73.24(10) . .
N2 B1 Li1 73.48(9) . .
N3 B1 H1A 110.3 . .
N2 B1 H1A 110.3 . .
Li1 B1 H1A 173.1 . .
N3 B1 H1B 110.3 . .
N2 B1 H1B 110.3 . .
Li1 B1 H1B 64.5 . .
H1A B1 H1B 108.5 . .
C25 C29 H29A 109.5 . .
C25 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C25 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C1 Li1 C2 148.67(14) . 2_656
C1 Li1 C2 103.04(12) . .
C2 Li1 C2 108.20(11) 2_656 .
C1 Li1 Li1 150.33(16) . 2_656
C2 Li1 Li1 57.90(10) 2_656 2_656
C2 Li1 Li1 52.32(10) . 2_656
C1 Li1 B1 60.69(9) . .
C2 Li1 B1 136.34(13) 2_656 .
C2 Li1 B1 59.45(8) . .
Li1 Li1 B1 90.24(11) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C2 1.3586(19) .
N3 C7 1.3777(19) .
N3 B1 1.559(2) .
N1 C1 1.3726(19) .
N1 C5 1.386(2) .
N1 C13 1.4435(18) .
N4 C2 1.3667(19) .
N4 C8 1.3829(19) .
N4 C22 1.440(2) .
N2 C1 1.358(2) .
N2 C6 1.3784(19) .
N2 B1 1.563(2) .
C1 Li1 2.133(3) .
C13 C14 1.390(2) .
C13 C18 1.398(2) .
C22 C23 1.395(2) .
C22 C27 1.398(2) .
C27 C26 1.392(2) .
C27 C30 1.504(2) .
C18 C17 1.395(2) .
C18 C21 1.496(2) .
C8 C7 1.344(2) .
C8 H8 0.9500 .
C7 H7 0.9500 .
C17 C16 1.386(2) .
C17 H17 0.9500 .
C2 Li1 2.181(3) 2_656
C2 Li1 2.335(3) .
C23 C24 1.389(2) .
C23 C28 1.503(2) .
C6 C5 1.348(2) .
C6 H6 0.9500 .
C14 C15 1.401(2) .
C14 C19 1.507(2) .
C16 C15 1.387(2) .
C16 C20 1.510(2) .
C5 H5 0.9500 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C15 H15 0.9500 .
C26 C25 1.390(2) .
C26 H26 0.9500 .
C24 C25 1.382(2) .
C24 H24 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C25 C29 1.510(3) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
B1 Li1 2.798(3) .
B1 H1A 0.9900 .
B1 H1B 0.9900 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
Li1 C2 2.181(3) 2_656
Li1 Li1 2.586(5) 2_656
