#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:14:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180031 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/25/7032518.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_7032518
loop_
_publ_author_name
'Behrle, Andrew C.'
'Levin, Jessica R.'
'Kim, Jee Eon'
'Drewett, Jonathan M.'
'Barnes, Charles L.'
'Schelter, Eric J.'
'Walensky, Justin R.'
_publ_section_title
;
 Stabilization of M(IV) = Ti, Zr, Hf, Ce, and Th using a selenium
 bis(phenolate) ligand.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2693
_journal_page_last               2702
_journal_paper_doi               10.1039/c4dt01798f
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C66 H88 Ce N2 O4 Se2'
_chemical_formula_sum            'C66 H88 Ce N2 O4 Se2'
_chemical_formula_weight         1271.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.8320(16)
_cell_length_b                   10.6765(7)
_cell_length_c                   26.0860(18)
_cell_measurement_temperature    100(2)
_cell_volume                     6214.0(7)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32803
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    1.951
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_correction_T_min  0.8288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0190P)²+13.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0601
_reflns_number_gt                5199
_reflns_number_total             6370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt01798f2.cif
_cod_data_source_block           Ce[ArOSeO]2(bipy)_Ar=2,4-tBu2C6H2
_cod_depositor_comments
'Adding full bibliography for 7032518--7032522.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7032518
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'
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
Ce1 Ce 0.5000 0.385553(19) 0.2500 0.01299(6) Uani 1 2 d S
Se1 Se 0.536279(11) 0.15022(2) 0.196408(10) 0.01422(7) Uani 1 1 d .
C15 C 0.55558(10) 0.3726(2) 0.14125(10) 0.0155(5) Uani 1 1 d .
O2 O 0.53249(7) 0.42738(16) 0.17849(7) 0.0162(4) Uani 1 1 d .
C19 C 0.59786(11) 0.3718(3) 0.06408(10) 0.0189(6) Uani 1 1 d .
H19 H 0.6095 0.4167 0.0364 0.023 Uiso 1 1 calc R
C16 C 0.56364(11) 0.2418(2) 0.14254(10) 0.0153(5) Uani 1 1 d .
C20 C 0.57251(11) 0.4400(2) 0.09977(10) 0.0155(5) Uani 1 1 d .
C27 C 0.49478(12) 0.6091(3) 0.08755(11) 0.0236(6) Uani 1 1 d .
H27A H 0.4882 0.6999 0.0865 0.035 Uiso 1 1 calc R
H27B H 0.4805 0.5734 0.1173 0.035 Uiso 1 1 calc R
H27C H 0.4728 0.5715 0.0548 0.035 Uiso 1 1 calc R
C25 C 0.56200(11) 0.5820(2) 0.09397(10) 0.0189(6) Uani 1 1 d .
C17 C 0.58805(11) 0.1777(3) 0.10587(11) 0.0191(6) Uani 1 1 d .
H17 H 0.5917 0.0891 0.1078 0.023 Uiso 1 1 calc R
C18 C 0.60717(12) 0.2425(3) 0.06636(11) 0.0204(6) Uani 1 1 d .
C26 C 0.58174(14) 0.6364(3) 0.04592(12) 0.0272(7) Uani 1 1 d .
H26A H 0.6247 0.6215 0.0490 0.041 Uiso 1 1 calc R
H26B H 0.5739 0.7267 0.0440 0.041 Uiso 1 1 calc R
H26C H 0.5592 0.5959 0.0141 0.041 Uiso 1 1 calc R
C24 C 0.65952(14) 0.2568(3) -0.01034(12) 0.0335(8) Uani 1 1 d .
H24A H 0.6261 0.3025 -0.0323 0.050 Uiso 1 1 calc R
H24B H 0.6801 0.2072 -0.0327 0.050 Uiso 1 1 calc R
H24C H 0.6877 0.3166 0.0101 0.050 Uiso 1 1 calc R
C23 C 0.58835(14) 0.0824(3) -0.00521(12) 0.0356(8) Uani 1 1 d .
H23A H 0.5748 0.0226 0.0183 0.053 Uiso 1 1 calc R
H23B H 0.6060 0.0367 -0.0308 0.053 Uiso 1 1 calc R
H23C H 0.5541 0.1318 -0.0236 0.053 Uiso 1 1 calc R
C21 C 0.63549(13) 0.1700(3) 0.02687(11) 0.0263(7) Uani 1 1 d .
C28 C 0.59748(13) 0.6504(3) 0.14253(11) 0.0246(6) Uani 1 1 d .
H28A H 0.6405 0.6374 0.1450 0.037 Uiso 1 1 calc R
H28B H 0.5861 0.6173 0.1741 0.037 Uiso 1 1 calc R
H28C H 0.5885 0.7402 0.1395 0.037 Uiso 1 1 calc R
N1 N 0.44620(10) 0.5983(2) 0.21727(9) 0.0230(5) Uani 1 1 d .
C2 C 0.60889(10) 0.1247(2) 0.24821(10) 0.0145(5) Uani 1 1 d .
C1 C 0.61837(10) 0.1996(2) 0.29370(10) 0.0137(5) Uani 1 1 d .
C3 C 0.64694(11) 0.0276(2) 0.24155(10) 0.0148(5) Uani 1 1 d .
H3 H 0.6391 -0.0192 0.2099 0.018 Uiso 1 1 calc R
C6 C 0.66410(11) 0.1602(2) 0.33672(10) 0.0157(5) Uani 1 1 d .
C4 C 0.69658(11) -0.0018(2) 0.28084(11) 0.0151(5) Uani 1 1 d .
C33 C 0.39657(13) 0.5929(3) 0.17981(12) 0.0301(7) Uani 1 1 d .
H33 H 0.3778 0.5139 0.1718 0.036 Uiso 1 1 calc R
C29 C 0.47232(14) 0.7105(3) 0.22891(12) 0.0287(7) Uani 1 1 d .
C22 C 0.68836(14) 0.0916(3) 0.05671(12) 0.0382(8) Uani 1 1 d .
H22A H 0.7177 0.1469 0.0786 0.057 Uiso 1 1 calc R
H22B H 0.7074 0.0478 0.0316 0.057 Uiso 1 1 calc R
H22C H 0.6737 0.0303 0.0790 0.057 Uiso 1 1 calc R
O1 O 0.58470(7) 0.30207(16) 0.29455(7) 0.0163(4) Uani 1 1 d .
C5 C 0.70214(11) 0.0638(2) 0.32761(11) 0.0168(6) Uani 1 1 d .
H5 H 0.7343 0.0415 0.3556 0.020 Uiso 1 1 calc R
C7 C 0.74234(11) -0.1006(2) 0.27188(11) 0.0185(6) Uani 1 1 d .
C9 C 0.79129(12) -0.0364(3) 0.24906(12) 0.0258(7) Uani 1 1 d .
H9A H 0.8201 -0.0992 0.2425 0.039 Uiso 1 1 calc R
H9B H 0.8120 0.0260 0.2741 0.039 Uiso 1 1 calc R
H9C H 0.7730 0.0051 0.2160 0.039 Uiso 1 1 calc R
C11 C 0.67329(12) 0.2206(2) 0.39150(11) 0.0205(6) Uani 1 1 d .
C10 C 0.77230(13) -0.1655(3) 0.32283(12) 0.0298(7) Uani 1 1 d .
H10A H 0.7417 -0.2063 0.3383 0.045 Uiso 1 1 calc R
H10B H 0.7939 -0.1035 0.3475 0.045 Uiso 1 1 calc R
H10C H 0.8006 -0.2286 0.3154 0.045 Uiso 1 1 calc R
C8 C 0.71268(13) -0.2004(3) 0.23312(12) 0.0280(7) Uani 1 1 d .
H8A H 0.7418 -0.2662 0.2306 0.042 Uiso 1 1 calc R
H8B H 0.6985 -0.1622 0.1985 0.042 Uiso 1 1 calc R
H8C H 0.6787 -0.2368 0.2453 0.042 Uiso 1 1 calc R
C14 C 0.70893(14) 0.1341(3) 0.43414(11) 0.0288(7) Uani 1 1 d .
H14A H 0.6895 0.0519 0.4320 0.043 Uiso 1 1 calc R
H14B H 0.7101 0.1708 0.4688 0.043 Uiso 1 1 calc R
H14C H 0.7499 0.1247 0.4288 0.043 Uiso 1 1 calc R
C12 C 0.61269(14) 0.2467(3) 0.40681(12) 0.0324(7) Uani 1 1 d .
H12A H 0.5908 0.3109 0.3835 0.049 Uiso 1 1 calc R
H12B H 0.6199 0.2763 0.4432 0.049 Uiso 1 1 calc R
H12C H 0.5890 0.1694 0.4035 0.049 Uiso 1 1 calc R
C13 C 0.70920(16) 0.3421(3) 0.39289(13) 0.0374(8) Uani 1 1 d .
H13A H 0.7498 0.3227 0.3886 0.056 Uiso 1 1 calc R
H13B H 0.7113 0.3842 0.4266 0.056 Uiso 1 1 calc R
H13C H 0.6895 0.3972 0.3644 0.056 Uiso 1 1 calc R
C30 C 0.44942(18) 0.8185(3) 0.20207(15) 0.0426(9) Uani 1 1 d .
H30 H 0.4690 0.8966 0.2103 0.051 Uiso 1 1 calc R
C32 C 0.37095(15) 0.6967(3) 0.15188(14) 0.0405(9) Uani 1 1 d .
H32 H 0.3355 0.6891 0.1254 0.049 Uiso 1 1 calc R
C31 C 0.39833(19) 0.8110(3) 0.16362(16) 0.0497(11) Uani 1 1 d .
H31 H 0.3820 0.8841 0.1452 0.060 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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
O2 Ce1 O2 156.52(9) 2_655 .
O2 Ce1 O1 96.46(6) 2_655 2_655
O2 Ce1 O1 92.91(6) . 2_655
O2 Ce1 O1 92.91(6) 2_655 .
O2 Ce1 O1 96.46(6) . .
O1 Ce1 O1 132.67(9) 2_655 .
O2 Ce1 N1 76.57(6) 2_655 2_655
O2 Ce1 N1 83.20(6) . 2_655
O1 Ce1 N1 144.03(7) 2_655 2_655
O1 Ce1 N1 83.24(7) . 2_655
O2 Ce1 N1 83.20(6) 2_655 .
O2 Ce1 N1 76.57(6) . .
O1 Ce1 N1 83.24(7) 2_655 .
O1 Ce1 N1 144.03(7) . .
N1 Ce1 N1 61.02(11) 2_655 .
O2 Ce1 Se1 136.50(4) 2_655 .
O2 Ce1 Se1 66.88(4) . .
O1 Ce1 Se1 73.90(4) 2_655 .
O1 Ce1 Se1 67.73(4) . .
N1 Ce1 Se1 134.40(5) 2_655 .
N1 Ce1 Se1 135.16(5) . .
O2 Ce1 Se1 66.88(4) 2_655 2_655
O2 Ce1 Se1 136.50(4) . 2_655
O1 Ce1 Se1 67.73(4) 2_655 2_655
O1 Ce1 Se1 73.90(4) . 2_655
N1 Ce1 Se1 135.16(5) 2_655 2_655
N1 Ce1 Se1 134.40(5) . 2_655
Se1 Ce1 Se1 70.320(11) . 2_655
C16 Se1 C2 102.74(10) . .
C16 Se1 Ce1 94.43(8) . .
C2 Se1 Ce1 94.11(8) . .
O2 C15 C16 119.1(2) . .
O2 C15 C20 123.1(2) . .
C16 C15 C20 117.7(2) . .
C15 O2 Ce1 141.87(16) . .
C18 C19 C20 124.5(3) . .
C17 C16 C15 122.9(2) . .
C17 C16 Se1 119.6(2) . .
C15 C16 Se1 117.46(18) . .
C19 C20 C15 117.5(2) . .
C19 C20 C25 121.7(2) . .
C15 C20 C25 120.8(2) . .
C26 C25 C27 107.4(2) . .
C26 C25 C28 107.4(2) . .
C27 C25 C28 109.9(2) . .
C26 C25 C20 112.8(2) . .
C27 C25 C20 109.2(2) . .
C28 C25 C20 110.1(2) . .
C16 C17 C18 120.2(2) . .
C17 C18 C19 117.1(2) . .
C17 C18 C21 119.4(3) . .
C19 C18 C21 123.5(2) . .
C24 C21 C23 109.2(3) . .
C24 C21 C18 112.3(2) . .
C23 C21 C18 109.1(2) . .
C24 C21 C22 107.6(2) . .
C23 C21 C22 109.2(3) . .
C18 C21 C22 109.4(2) . .
C33 N1 C29 118.2(3) . .
C33 N1 Ce1 117.75(19) . .
C29 N1 Ce1 122.75(19) . .
C3 C2 C1 122.8(2) . .
C3 C2 Se1 119.18(19) . .
C1 C2 Se1 117.82(18) . .
O1 C1 C2 119.4(2) . .
O1 C1 C6 123.7(2) . .
C2 C1 C6 116.9(2) . .
C2 C3 C4 120.7(2) . .
C5 C6 C1 117.4(2) . .
C5 C6 C11 119.9(2) . .
C1 C6 C11 122.7(2) . .
C5 C4 C3 116.1(2) . .
C5 C4 C7 122.8(2) . .
C3 C4 C7 121.1(2) . .
N1 C33 C32 123.4(3) . .
N1 C29 C30 121.5(3) . .
N1 C29 C29 115.68(18) . 2_655
C30 C29 C29 122.8(2) . 2_655
C1 O1 Ce1 139.28(16) . .
C4 C5 C6 125.2(2) . .
C8 C7 C10 108.3(2) . .
C8 C7 C9 108.2(2) . .
C10 C7 C9 108.2(2) . .
C8 C7 C4 111.1(2) . .
C10 C7 C4 111.9(2) . .
C9 C7 C4 109.1(2) . .
C13 C11 C14 107.0(2) . .
C13 C11 C6 110.1(2) . .
C14 C11 C6 111.5(2) . .
C13 C11 C12 110.2(2) . .
C14 C11 C12 106.7(2) . .
C6 C11 C12 111.2(2) . .
C31 C30 C29 119.4(3) . .
C31 C32 C33 118.1(4) . .
C30 C31 C32 119.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ce1 O2 2.1947(17) 2_655
Ce1 O2 2.1947(17) .
Ce1 O1 2.2205(17) 2_655
Ce1 O1 2.2205(17) .
Ce1 N1 2.637(2) 2_655
Ce1 N1 2.637(2) .
Ce1 Se1 3.0732(3) .
Ce1 Se1 3.0732(3) 2_655
Se1 C16 1.922(3) .
Se1 C2 1.923(2) .
C15 O2 1.334(3) .
C15 C16 1.408(3) .
C15 C20 1.420(4) .
C19 C18 1.396(4) .
C19 C20 1.400(4) .
C16 C17 1.386(4) .
C20 C25 1.537(4) .
C27 C25 1.536(3) .
C25 C26 1.534(4) .
C25 C28 1.536(4) .
C17 C18 1.387(4) .
C18 C21 1.537(4) .
C24 C21 1.526(4) .
C23 C21 1.534(4) .
C21 C22 1.538(4) .
N1 C33 1.331(4) .
N1 C29 1.344(4) .
C2 C3 1.387(3) .
C2 C1 1.409(4) .
C1 O1 1.340(3) .
C1 C6 1.424(4) .
C3 C4 1.393(4) .
C6 C5 1.399(4) .
C6 C11 1.541(4) .
C4 C5 1.389(4) .
C4 C7 1.537(3) .
C33 C32 1.386(4) .
C29 C30 1.391(4) .
C29 C29 1.489(7) 2_655
C7 C8 1.525(4) .
C7 C10 1.526(4) .
C7 C9 1.535(4) .
C11 C13 1.531(4) .
C11 C14 1.539(4) .
C11 C12 1.545(4) .
C30 C31 1.370(5) .
C32 C31 1.376(5) .
