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_4038650
_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         'C10 H14 O'
_chemical_formula_sum            'C10 H14 O'
_chemical_formula_weight         150.21
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2177(4)
_cell_length_b                   12.0514(4)
_cell_length_c                   12.2819(4)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.62
_cell_volume                     1808.36(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      120.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23658
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.272
_diffrn_reflns_theta_min         3.599
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6393
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0522
_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/[\s^2^(Fo^2^)+(0.0418P)^2^+0.8092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5612
_reflns_number_total             6393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00877_si_005.cif
_cod_data_source_block           2_a_pl
_cod_database_code               4038650
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(4)
 -0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O4(H4), O2(H), O1(H1), O3(HN)
3.b Ternary CH refined with riding coordinates:
 C32(H32), C22(HD), C2(H2), C12(HR)
3.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C35(H35), C27(HE), C25(HF), C26(HG), C7(H7), C6(H6),
 C5(H5), C17(HS), C16(HW), C15(HX)
3.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C31(H31A,H31B,H31C), C21(HA,HB,HC),
 C30(HH,HI,HJ), C29(HK,HL,HM), C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C9(H9A,H9B,
 H9C), C11(HO,HP,HQ), C20(HT,HU,HV), C19(HY,HZ,H0AA)
;
_shelx_res_checksum              697
_shelx_hkl_checksum              11420
_olex2_submission_special_instructions 'No special instructions were received'