Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones.
Wang, Weifan; Shen, Xingchao; Zhao, Fengyi; Jiang, Huan; Yao, Weiwei; Pullarkat, Sumod A.; Xu, Li; Ma, Mengtao; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02076

data_4033259
_publ_section_title
;
 Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02076
_journal_year                    2017
_chemical_formula_moiety         'C100 H104 I N2 O2 Yb, 2(C7 H8)'
_chemical_formula_sum            'C114 H120 I N2 O2 Yb'
_chemical_formula_weight         1850.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2807(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7803(6)
_cell_length_b                   25.6504(8)
_cell_length_c                   20.8183(6)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    131(2)
_cell_measurement_theta_max      28.301
_cell_measurement_theta_min      2.293
_cell_volume                     9487.1(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130.99
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            69820
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.113
_exptl_absorpt_coefficient_mu    1.363
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             3828
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         1.782
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1099
_refine_ls_number_reflns         18573
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+2.0770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13828
_reflns_number_total             18573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02076_si_002.cif
_cod_data_source_block           mo_20150409b_0m
_cod_database_code               4033259
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C108) \\sim Ueq, Uanis(C109) \\sim Ueq, Uanis(C110) \\sim Ueq,
Uanis(C111) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C113) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C22(H22), C35(H35), C38(H38), C72(H72), C85(H85), C88(H88)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C15(H15), C18(H18), C20(H20), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50), C53(H53), C55(H55), C65(H65), C68(H68), C70(H70), C74(H74),
  C75(H75), C76(H76), C77(H77), C78(H78), C80(H80), C81(H81), C82(H82),
 C83(H83), C84(H84), C90(H90), C91(H91), C92(H92), C93(H93), C94(H94), C96(H96),
  C97(H97), C98(H98), C99(H99), C100(H100), C101(H101), C102(H102), C104(H104),
 C105(H105), C106(H106), C108(H108), C109(H109), C110(H110), C111(H111),
 C112(H112)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C62(H62A,
 H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C86(H86A,H86B,H86C),
 C87(H87A,H87B,H87C), C107(H10D,H10E,H10F), C114(H11A,H11B,H11C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'