Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth Metal Complexes Containing Trost Ligands.
Sun, Yuli; Lu, Chengrong; Zhao, Bei; Xue, Mingqiang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00877

data_4038651
_publ_section_title
;
 Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth Metal
 Complexes Containing Trost Ligands.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00877
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C86 H86 La2 N4 O6'
_chemical_formula_sum            'C86 H86 La2 N4 O6'
_chemical_formula_weight         1549.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.1240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.7694(6)
_cell_length_b                   26.0930(11)
_cell_length_c                   14.2594(7)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.33
_cell_volume                     4638.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  none
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            107036
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.219
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.610
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.025(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         16296
_refine_ls_number_restraints     543
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                13988
_reflns_number_total             16296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00877_si_004.cif
_cod_data_source_block           20161126a_0m_sq
_cod_database_code               4038651
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.975(17)
 0.025(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C65, C66
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C66, C67
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C4AA \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65
\\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73
\\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81
\\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C12(H12), C29(H29), C55(H55), C73(H73)
5.b Secondary CH2 refined with riding coordinates:
 C4AA(H4AA,H4AB), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C54(H54A,H54B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,
 H71B), C72(H72A,H72B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C33(H33), C34(H34), C35(H35), C36(H36),
  C37(H37), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46),
 C50(H50), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C64(H64), C65(H65),
  C66(H66), C67(H67), C68(H68), C76(H76), C77(H77), C78(H78), C79(H79),
 C80(H80), C82(H82), C83(H83), C84(H84), C85(H85), C86(H86)
5.d Fitted hexagon refined as free rotating group:
 C63(C64,C65,C66,C67,C68)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              42075
_shelx_hkl_checksum              65488
_shelx_fab_checksum              28517
_olex2_submission_special_instructions 'No special instructions were received'