Kinetic resolution via supramolecular iminium catalysis: multiactivation enables the asymmetric synthesis of β-aryl substituted aldehydes and densely functionalized cyclohexanes.
Jia, Zhi-Long; Wang, Yao; Xu, Guo-Qiang; Xu, Peng-Fei; Chemical communications (Cambridge, England) 53 (2017) 4938–4941; doi:10.1039/c7cc01625e

data_7120092
_publ_section_title
;
 Kinetic resolution via supramolecular iminium catalysis: multiactivation
 enables the asymmetric synthesis of \b-aryl substituted aldehydes and
 densely functionalized cyclohexanes.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4938
_journal_page_last               4941
_journal_paper_doi               10.1039/c7cc01625e
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H25 Cl O3'
_chemical_formula_sum            'C28 H25 Cl O3'
_chemical_formula_weight         444.93
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-12 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.733(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5747(5)
_cell_length_b                   16.8602(9)
_cell_length_c                   10.7211(7)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      21.4730
_cell_measurement_theta_min      3.9310
_cell_volume                     1185.92(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -15.00   19.65   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   30.0000 33

  2 omega  -45.00   45.30   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   90.0000 86

  3 omega  -34.00   94.10   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000   60.0000 122

  4 omega   -1.00   93.50   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -120.0000 90

  5 omega   77.00  102.20   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   90.0000 24

  6 omega   -9.00   19.35   1.0500   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0781125000
_diffrn_orient_matrix_UB_12      0.0011523000
_diffrn_orient_matrix_UB_13      -0.0487796000
_diffrn_orient_matrix_UB_21      -0.0740041000
_diffrn_orient_matrix_UB_22      -0.0071836000
_diffrn_orient_matrix_UB_23      0.0439705000
_diffrn_orient_matrix_UB_31      -0.0106490000
_diffrn_orient_matrix_UB_32      0.0414356000
_diffrn_orient_matrix_UB_33      0.0090030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7996
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                2772
_reflns_number_total             4371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc01625e2.cif
_cod_data_source_block           zhaochg_0627
_cod_original_cell_volume        1185.93(14)
_cod_database_code               7120092
_chemical_oxdiff_formula         'C30 S8 H20 I2'
_reflns_odcompleteness_completeness 99.76
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_olex2_date_sample_data_collection 2016-06-28
_olex2_submission_special_instructions 'No special instructions were received'