#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:29:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179020 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/18/4121859.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_4121859
loop_
_publ_author_name
'Robinson, Jerome R.'
'Fan, Xinyuan'
'Yadav, Jagjit'
'Carroll, Patrick J.'
'Wooten, Alfred J.'
'Pericàs, Miquel A'
'Schelter, Eric J.'
'Walsh, Patrick J.'
_publ_section_title
;
 Air- and Water-Tolerant Rare Earth Guanidinium BINOLate Complexes as
 Practical Precatalysts in Multifunctional Asymmetric Catalysis.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8034
_journal_paper_doi               10.1021/ja502568g
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C78 H84 Cl6 N9 O6 Yb'
_chemical_formula_weight         1629.28
_space_group_IT_number           197
_symmetry_cell_setting           cubic
_symmetry_Int_Tables_number      197
_symmetry_space_group_name_Hall  'I 2 2 3'
_symmetry_space_group_name_H-M   'I 2 3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.5542(10)
_cell_length_b                   26.5542(10)
_cell_length_c                   26.5542(10)
_cell_measurement_temperature    100(1)
_cell_volume                     18724.0(12)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            121581
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.217
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6680
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         7189
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.796
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0429
_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)+(0.1013P)²+100.6265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                6831
_reflns_number_total             7189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502568g_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

 Adding full bibliography for 4121856--4121859.cif.
;
_cod_original_sg_symbol_H-M      'I 23     '
_cod_database_code               4121859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'y, z, x'
'z, x, y'
'x, -y, -z'
'y, -z, -x'
'z, -x, -y'
'-y, z, -x'
'-z, x, -y'
'-z, -x, y'
'-x, -y, z'
'-y, -z, x'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'y+1/2, z+1/2, x+1/2'
'z+1/2, x+1/2, y+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, -z+1/2, -x+1/2'
'z+1/2, -x+1/2, -y+1/2'
'-y+1/2, z+1/2, -x+1/2'
'-z+1/2, x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, -z+1/2, x+1/2'
'-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
Yb1 Yb 0.291623(6) 0.291623(6) 0.291623(6) 0.03069(9) Uani 1 3 d S
O1 O 0.20928(12) 0.27912(10) 0.30146(10) 0.0330(5) Uani 1 1 d .
O2 O 0.26982(11) 0.36754(11) 0.31756(12) 0.0356(6) Uani 1 1 d .
C1 C 0.17811(15) 0.31045(16) 0.27821(15) 0.0323(8) Uani 1 1 d .
C2 C 0.15810(15) 0.29698(18) 0.23098(16) 0.0363(8) Uani 1 1 d .
H2 H 0.1654 0.2653 0.2179 0.048 Uiso 1 1 calc R
C3 C 0.12816(16) 0.3290(2) 0.20375(17) 0.0417(9) Uani 1 1 d .
H3 H 0.1152 0.3188 0.1729 0.055 Uiso 1 1 calc R
C4 C 0.11700(15) 0.3775(2) 0.22257(17) 0.0409(10) Uani 1 1 d .
C5 C 0.08638(18) 0.4131(2) 0.1948(2) 0.0500(13) Uani 1 1 d .
H5 H 0.0747 0.4046 0.1629 0.067 Uiso 1 1 calc R
C6 C 0.07436(18) 0.4587(2) 0.2146(3) 0.0576(16) Uani 1 1 d .
H6 H 0.0542 0.4809 0.1964 0.077 Uiso 1 1 calc R
C7 C 0.09165(19) 0.4722(2) 0.2610(2) 0.0500(12) Uani 1 1 d .
H7 H 0.0831 0.5036 0.2738 0.066 Uiso 1 1 calc R
C8 C 0.12158(17) 0.44041(16) 0.2895(2) 0.0445(10) Uani 1 1 d .
H8 H 0.1334 0.4509 0.3208 0.059 Uiso 1 1 calc R
C9 C 0.13426(16) 0.39134(17) 0.27083(17) 0.0362(9) Uani 1 1 d .
C10 C 0.16516(15) 0.35767(15) 0.29885(16) 0.0325(8) Uani 1 1 d .
C11 C 0.18565(17) 0.37104(15) 0.34946(16) 0.0334(8) Uani 1 1 d .
C12 C 0.15389(18) 0.37743(16) 0.39226(18) 0.0386(9) Uani 1 1 d .
C13 C 0.10027(18) 0.37311(16) 0.38891(19) 0.0402(9) Uani 1 1 d .
H13 H 0.0857 0.3657 0.3579 0.054 Uiso 1 1 calc R
C14 C 0.0697(2) 0.37959(19) 0.4300(2) 0.0480(11) Uani 1 1 d .
H14 H 0.0349 0.3764 0.4267 0.064 Uiso 1 1 calc R
C15 C 0.0907(2) 0.3911(2) 0.4772(2) 0.0532(13) Uani 1 1 d .
H15 H 0.0697 0.3966 0.5047 0.071 Uiso 1 1 calc R
C16 C 0.1416(3) 0.3943(2) 0.4827(2) 0.0586(14) Uani 1 1 d .
H16 H 0.1554 0.4006 0.5143 0.078 Uiso 1 1 calc R
C17 C 0.1740(2) 0.3879(2) 0.44006(19) 0.0479(11) Uani 1 1 d .
C18 C 0.2269(2) 0.3922(3) 0.4453(2) 0.0593(15) Uani 1 1 d .
H18 H 0.2409 0.3993 0.4767 0.079 Uiso 1 1 calc R
C19 C 0.2579(2) 0.3859(2) 0.4040(2) 0.0497(12) Uani 1 1 d .
H19 H 0.2926 0.3889 0.4081 0.066 Uiso 1 1 calc R
C20 C 0.23811(17) 0.37507(17) 0.35548(17) 0.0367(9) Uani 1 1 d .
N1 N 0.22018(14) 0.25631(14) 0.40185(13) 0.0361(8) Uani 1 1 d .
H1A H 0.2066 0.2580 0.3725 0.048 Uiso 1 1 calc R
H1B H 0.2515 0.2636 0.4056 0.048 Uiso 1 1 calc R
N2 N 0.14473(14) 0.23130(14) 0.43509(14) 0.0373(8) Uani 1 1 d .
N3 N 0.21499(17) 0.23919(16) 0.48649(14) 0.0443(9) Uani 1 1 d .
C21 C 0.19345(17) 0.24271(16) 0.44047(16) 0.0354(9) Uani 1 1 d .
C22 C 0.12420(18) 0.22690(18) 0.38475(18) 0.0405(9) Uani 1 1 d .
H22A H 0.1161 0.2598 0.3721 0.061 Uiso 1 1 calc R
H22B H 0.0943 0.2066 0.3857 0.061 Uiso 1 1 calc R
H22C H 0.1486 0.2113 0.3631 0.061 Uiso 1 1 calc R
C23 C 0.1079(2) 0.24633(19) 0.4738(2) 0.0468(11) Uani 1 1 d .
H23A H 0.1252 0.2531 0.5048 0.070 Uiso 1 1 calc R
H23B H 0.0841 0.2196 0.4788 0.070 Uiso 1 1 calc R
H23C H 0.0905 0.2761 0.4629 0.070 Uiso 1 1 calc R
C24 C 0.2005(3) 0.2014(2) 0.52273(17) 0.0552(14) Uani 1 1 d .
H24A H 0.1703 0.1850 0.5116 0.083 Uiso 1 1 calc R
H24B H 0.1946 0.2171 0.5548 0.083 Uiso 1 1 calc R
H24C H 0.2270 0.1771 0.5260 0.083 Uiso 1 1 calc R
C25 C 0.2651(2) 0.2599(2) 0.4947(2) 0.0557(13) Uani 1 1 d .
H25A H 0.2899 0.2374 0.4810 0.084 Uiso 1 1 calc R
H25B H 0.2709 0.2640 0.5301 0.084 Uiso 1 1 calc R
H25C H 0.2677 0.2921 0.4783 0.084 Uiso 1 1 calc R
C26 C 0.0139(3) 0.0884(4) 0.3936(3) 0.123(5) Uani 1 1 d D
H26A H 0.0143 0.0519 0.3941 0.163 Uiso 1 1 calc R
H26B H -0.0205 0.0993 0.3990 0.163 Uiso 1 1 calc R
Cl1 Cl 0.03410(16) 0.10943(15) 0.33357(19) 0.1614(16) Uani 1 1 d D
Cl2 Cl 0.05223(14) 0.11131(12) 0.44414(16) 0.1346(11) Uani 1 1 d 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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 Yb1 O2 92.09(11) 2 3
O2 Yb1 O2 92.09(11) 2 .
O2 Yb1 O2 92.09(11) 3 .
O2 Yb1 O1 166.88(11) 2 .
O2 Yb1 O1 99.21(11) 3 .
O2 Yb1 O1 80.91(10) . .
O2 Yb1 O1 99.21(11) 2 3
O2 Yb1 O1 80.91(10) 3 3
O2 Yb1 O1 166.88(11) . 3
O1 Yb1 O1 89.22(10) . 3
O2 Yb1 O1 80.91(10) 2 2
O2 Yb1 O1 166.88(11) 3 2
O2 Yb1 O1 99.21(11) . 2
O1 Yb1 O1 89.22(10) . 2
O1 Yb1 O1 89.22(10) 3 2
O2 Yb1 C1 117.00(11) 2 3
O2 Yb1 C1 68.33(11) 3 3
O2 Yb1 C1 144.46(11) . 3
O1 Yb1 C1 73.81(10) . 3
O1 Yb1 C1 22.44(11) 3 3
O1 Yb1 C1 104.91(11) 2 3
O2 Yb1 C1 144.46(11) 2 .
O2 Yb1 C1 117.00(11) 3 .
O2 Yb1 C1 68.33(11) . .
O1 Yb1 C1 22.44(11) . .
O1 Yb1 C1 104.91(11) 3 .
O1 Yb1 C1 73.81(10) 2 .
C1 Yb1 C1 93.71(11) 3 .
O2 Yb1 C1 68.33(11) 2 2
O2 Yb1 C1 144.46(11) 3 2
O2 Yb1 C1 117.00(11) . 2
O1 Yb1 C1 104.91(11) . 2
O1 Yb1 C1 73.81(10) 3 2
O1 Yb1 C1 22.44(11) 2 2
C1 Yb1 C1 93.71(11) 3 2
C1 Yb1 C1 93.71(11) . 2
O2 Yb1 C20 80.36(11) 2 3
O2 Yb1 C20 20.91(12) 3 3
O2 Yb1 C20 109.61(12) . 3
O1 Yb1 C20 112.40(11) . 3
O1 Yb1 C20 66.20(11) 3 3
O1 Yb1 C20 145.98(11) 2 3
C1 Yb1 C20 60.20(11) 3 3
C1 Yb1 C20 133.34(11) . 3
C1 Yb1 C20 123.56(11) 2 3
O2 Yb1 C20 109.61(12) 2 .
O2 Yb1 C20 80.36(11) 3 .
O2 Yb1 C20 20.91(12) . .
O1 Yb1 C20 66.20(11) . .
O1 Yb1 C20 145.98(11) 3 .
O1 Yb1 C20 112.40(11) 2 .
C1 Yb1 C20 123.56(11) 3 .
C1 Yb1 C20 60.20(11) . .
C1 Yb1 C20 133.34(11) 2 .
C20 Yb1 C20 100.58(10) 3 .
O2 Yb1 C20 20.91(12) 2 2
O2 Yb1 C20 109.61(12) 3 2
O2 Yb1 C20 80.36(11) . 2
O1 Yb1 C20 145.98(11) . 2
O1 Yb1 C20 112.40(11) 3 2
O1 Yb1 C20 66.20(11) 2 2
C1 Yb1 C20 133.34(11) 3 2
C1 Yb1 C20 123.56(11) . 2
C1 Yb1 C20 60.20(11) 2 2
C20 Yb1 C20 100.58(10) 3 2
C20 Yb1 C20 100.58(10) . 2
C1 O1 Yb1 117.7(2) . .
C20 O2 Yb1 122.7(3) . .
O1 C1 C2 119.4(4) . .
O1 C1 C10 121.9(4) . .
C2 C1 C10 118.7(4) . .
O1 C1 Yb1 39.87(17) . .
C2 C1 Yb1 115.6(3) . .
C10 C1 Yb1 109.8(3) . .
C3 C2 C1 122.1(4) . .
C2 C3 C4 120.0(4) . .
C3 C4 C9 119.4(4) . .
C3 C4 C5 122.2(5) . .
C9 C4 C5 118.3(5) . .
C6 C5 C4 121.2(5) . .
C7 C6 C5 120.3(5) . .
C6 C7 C8 121.9(5) . .
C7 C8 C9 119.9(5) . .
C10 C9 C4 119.9(4) . .
C10 C9 C8 121.7(4) . .
C4 C9 C8 118.4(4) . .
C9 C10 C1 119.7(4) . .
C9 C10 C11 122.1(4) . .
C1 C10 C11 118.2(4) . .
C20 C11 C12 119.1(4) . .
C20 C11 C10 118.8(4) . .
C12 C11 C10 122.0(4) . .
C17 C12 C11 121.3(5) . .
C17 C12 C13 116.8(4) . .
C11 C12 C13 122.0(4) . .
C14 C13 C12 122.0(5) . .
C13 C14 C15 120.1(5) . .
C16 C15 C14 120.2(5) . .
C15 C16 C17 120.2(6) . .
C12 C17 C18 118.8(5) . .
C12 C17 C16 120.7(5) . .
C18 C17 C16 120.5(5) . .
C19 C18 C17 120.1(5) . .
C18 C19 C20 121.7(5) . .
O2 C20 C11 122.0(4) . .
O2 C20 C19 118.9(4) . .
C11 C20 C19 119.0(4) . .
O2 C20 Yb1 36.39(19) . .
C11 C20 Yb1 109.5(3) . .
C19 C20 Yb1 117.8(3) . .
C21 N2 C22 118.8(4) . .
C21 N2 C23 120.4(4) . .
C22 N2 C23 114.6(4) . .
C21 N3 C24 122.6(5) . .
C21 N3 C25 119.7(4) . .
C24 N3 C25 114.0(4) . .
N1 C21 N2 120.5(4) . .
N1 C21 N3 120.1(4) . .
N2 C21 N3 119.4(4) . .
Cl1 C26 Cl2 113.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Yb1 O2 2.208(3) 2
Yb1 O2 2.208(3) 3
Yb1 O2 2.208(3) .
Yb1 O1 2.227(3) .
Yb1 O1 2.227(3) 3
Yb1 O1 2.227(3) 2
Yb1 C1 3.076(4) 3
Yb1 C1 3.076(4) .
Yb1 C1 3.076(4) 2
Yb1 C20 3.131(5) 3
Yb1 C20 3.131(5) .
Yb1 C20 3.131(5) 2
O1 C1 1.326(5) .
O2 C20 1.328(5) .
C1 C2 1.408(6) .
C1 C10 1.411(6) .
C2 C3 1.370(7) .
C3 C4 1.413(8) .
C4 C9 1.410(7) .
C4 C5 1.449(7) .
C5 C6 1.358(9) .
C6 C7 1.362(9) .
C7 C8 1.386(7) .
C8 C9 1.434(7) .
C9 C10 1.423(6) .
C10 C11 1.493(6) .
C11 C20 1.406(6) .
C11 C12 1.426(6) .
C12 C17 1.405(7) .
C12 C13 1.431(7) .
C13 C14 1.372(7) .
C14 C15 1.404(9) .
C15 C16 1.364(9) .
C16 C17 1.432(8) .
C17 C18 1.418(9) .
C18 C19 1.381(8) .
C19 C20 1.422(6) .
N1 C21 1.298(6) .
N2 C21 1.336(6) .
N2 C22 1.448(6) .
N2 C23 1.473(5) .
N3 C21 1.353(6) .
N3 C24 1.442(6) .
N3 C25 1.458(7) .
C26 Cl1 1.772(8) .
C26 Cl2 1.791(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 1.97 2.749(5) 150.1 .
N1 H1B O2 0.86 2.03 2.765(5) 142.8 3
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 2108 255 ' '
2 0.500 0.000 0.000 45 16 ' '
3 0.500 0.000 0.500 45 16 ' '
4 0.000 0.000 0.500 45 16 ' '
5 0.500 0.500 0.500 2108 255 ' '
6 0.000 0.500 0.500 45 16 ' '
7 0.000 0.500 0.000 45 16 ' '
8 0.500 0.500 0.000 45 16 ' '
