Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis.
Bora, Pranjal; Jakkampudi, Satish; Parella, Ramarao; Sakkani, Nagaraju; Dai, Qipu; Bihani, Manisha; Arman, Hadi D.; Zhao, John C.-G.; Chemical communications (Cambridge, England) 57 (2021) 5334–5337; doi:10.1039/d1cc01020d

data_7128238
_publ_section_title
;
 Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using
 the modularly designed organocatalysts upon switching on their iminium
 catalysis.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5334
_journal_page_last               5337
_journal_paper_doi               10.1039/d1cc01020d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H24 O4'
_chemical_formula_sum            'C23 H24 O4'
_chemical_formula_weight         364.42
_chemical_name_systematic
(1R,2R,6R)-2-(4-methoxyphenyl)-6-[(E)-4-methoxystyryl]-4-oxocyclohexane-1-carbaldehyde
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-08 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.118(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.4116(11)
_cell_length_b                   6.0927(2)
_cell_length_c                   10.9457(3)
_cell_measurement_reflns_used    9157
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      23.6490
_cell_measurement_theta_min      2.7700
_cell_volume                     1936.64(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -96.00  17.00   1.00   29.00    --   -7.50 -38.00 -90.00  113
  2  \w    -46.00  81.00   1.00   29.00    --   -7.50  19.00-180.00  127
  3  \w    -96.00  31.00   1.00   29.00    --   -7.50 -19.00 -30.00  127
  4  \w    -26.00  94.00   1.00   29.00    --    4.20  57.00-120.00  120
  5  \w    -40.00  81.00   1.00   29.00    --   -7.50  72.00-120.00  121
  6  \w    -40.00  81.00   1.00   29.00    --   -7.50  72.00  30.00  121
  7  \w    -96.00 -35.00   1.00   29.00    --   -7.50 -72.00 120.00   61
  8  \w    -37.00  81.00   1.00   29.00    --   -7.50  57.00   0.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0070352000
_diffrn_orient_matrix_UB_12      0.1047881000
_diffrn_orient_matrix_UB_13      0.0241512000
_diffrn_orient_matrix_UB_21      -0.0232714000
_diffrn_orient_matrix_UB_22      0.0353478000
_diffrn_orient_matrix_UB_23      -0.0095798000
_diffrn_orient_matrix_UB_31      -0.0023099000
_diffrn_orient_matrix_UB_32      -0.0363858000
_diffrn_orient_matrix_UB_33      0.0602654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            46751
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.806
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, hexane'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0150P)^2^+3.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3296
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01020d2.cif
_cod_data_source_block           MMOCC
_cod_depositor_comments
'Adding full bibliography for 7128238--7128240.cif.'
_cod_database_code               7128238
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C20H20O4
_chemical_oxdiff_usercomment     PB-3-OMe
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C16(H16), C22(H22), C7(H7), C8(H8), C21(H21), C10(H10),
 C14(H14), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C15(H15A,H15B,H15C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.100
_oxdiff_exptl_absorpt_empirical_full_min 0.932