Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones <i>via</i> a hydrogenation/isomerization cascade.
Wang, Kun; Niu, Saisai; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Li, Hongfeng; Wang, Chao; Chemical communications (Cambridge, England) 60 (2024) 4338–4341; doi:10.1039/d4cc00356j

data_7132857
_publ_section_title
;
 Ru-catalyzed asymmetric hydrogenation of &#x3b1;,&#x3b2;-unsaturated
 ketones <i>via</i> a hydrogenation/isomerization cascade.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4338
_journal_page_last               4341
_journal_paper_doi               10.1039/d4cc00356j
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 O'
_chemical_formula_sum            'C17 H18 O'
_chemical_formula_weight         238.31
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc288pt2
_audit_creation_date             2020-11-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-07-01 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.369(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5667(13)
_cell_length_b                   5.2499(6)
_cell_length_c                   12.1291(14)
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    205.0
_cell_measurement_theta_max      68.491
_cell_measurement_theta_min      4.104
_cell_volume                     654.08(13)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      205.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9493
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.485
_diffrn_reflns_theta_min         4.104
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0771 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.1705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2323
_reflns_number_total             2357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00356j2.cif
_cod_data_source_block           s
_cod_depositor_comments          'Adding full bibliography for 7132857.cif.'
_cod_database_code               7132857
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C00A(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C002(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00H), C00D(H00I), C00E(H00J), C00F(H00K),
 C00G(H00L), C00H(H00M), C00I(H00N)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              96749
_olex2_submission_special_instructions 'No special instructions were received'