Chemoselective Luche-type reduction of α,β-unsaturated ketones by aluminium hydride catalysis.
Yan, Ben; Ma, Xiaoli; Pang, Ziyuan; Yang, Zhi; Dalton transactions (Cambridge, England : 2003) 53 (2024) 4127–4131; doi:10.1039/d3dt03987k

data_7715368
_publ_section_title
;
 Chemoselective Luche-type reduction of &#x3b1;,&#x3b2;-unsaturated
 ketones by aluminium hydride catalysis.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4127
_journal_page_last               4131
_journal_paper_doi               10.1039/d3dt03987k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C44 H53 Al N2 O2'
_chemical_formula_sum            'C44 H52 Al N2 O2'
_chemical_formula_weight         667.85
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.076(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3973(4)
_cell_length_b                   8.7653(3)
_cell_length_c                   38.0302(14)
_cell_measurement_reflns_used    11808
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      30.6170
_cell_measurement_theta_min      2.3930
_cell_volume                     3799.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.729
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -33.00  -8.68   0.38    1.15    --   -6.91 -50.00 -74.00   64
  2  \w    -18.00  34.06   0.38    1.15    --    3.55 -99.00  30.00  137
  3  \w    -78.00 -51.78   0.38    1.15    --   -6.91 -50.00 -74.00   69
  4  \w     -7.00  32.14   0.38    1.15    --    3.55 -99.00-150.00  103
  5  \w      6.00  34.12   0.38    1.15    --    3.55 -99.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151766000
_diffrn_orient_matrix_UB_12      0.0491417000
_diffrn_orient_matrix_UB_13      0.0141208000
_diffrn_orient_matrix_UB_21      -0.0589848000
_diffrn_orient_matrix_UB_22      -0.0015091000
_diffrn_orient_matrix_UB_23      0.0059315000
_diffrn_orient_matrix_UB_31      0.0129462000
_diffrn_orient_matrix_UB_32      -0.0642564000
_diffrn_orient_matrix_UB_33      0.0106298000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.729
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            22198
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.729
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.001
_diffrn_reflns_theta_min         2.384
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.86a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             1436
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         8833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0449P)^2^+1.0101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6731
_reflns_number_total             8833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03987k2.cif
_cod_data_source_block           al-h_auto
_cod_database_code               7715368
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C H N Al'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_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.a Ternary CH refined with riding coordinates:
 C21(H21), C18(H18), C40(H40), C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C25(H25), C29(H29), C16(H16), C27(H27), C48(H48), C28(H28), C15(H15),
 C14(H14), C26(H26), C34(H34), C35(H35), C44(H44), C33(H33), C47(H47), C45(H45),
  C46(H46)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C49(H49A,H49B,
 H49C), C20(H20A,H20B,H20C), C42(H42A,H42B,H42C), C19(H19A,H19B,H19C), C39(H39A,
 H39B,H39C), C41(H41A,H41B,H41C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              62484
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.752