A new chiral C1-symmetric NHC-catalyzed addition to alpha-aryl substituted alpha,beta-disubstituted enals: enantioselective synthesis of fully functionalized dihydropyranones
Hong Lu; Jin-Yu Liu; Chen-Guang Li; Jun-Bing Lin; Yong-Min Liang; Peng-Fei Xu; Chem.Commun. 51 (2015) 4473–; doi:10.1039/C5cc00118H

data_7116647
_publ_section_title
;
 A new chiral C1-symmetric NHC-catalyzed addition to alpha-aryl
 substituted alpha,beta-disubstituted enals: enantioselective synthesis of
 fully functionalized dihydropyranones
;
_journal_name_full               Chem.Commun.
_journal_page_first              4473
_journal_paper_doi               10.1039/C5cc00118H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H23 Cl O8'
_chemical_formula_sum            'C24 H23 Cl O8'
_chemical_formula_weight         474.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_audit_update_record
;
2014-12-02 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                113.081(12)
_cell_angle_beta                 96.350(11)
_cell_angle_gamma                102.204(14)
_cell_formula_units_Z            2
_cell_length_a                   9.2814(16)
_cell_length_b                   11.7110(17)
_cell_length_c                   12.1339(13)
_cell_measurement_reflns_used    1195
_cell_measurement_temperature    291.89(10)
_cell_measurement_theta_max      20.6310
_cell_measurement_theta_min      3.8420
_cell_volume                     1158.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -19.00   24.20   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -120.0000 24

  2 omega  -49.00   41.00   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000   60.0000 50

  3 omega    0.00   88.20   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000 -150.0000 49

  4 omega    1.00   37.00   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000   60.0000 20

  5 omega   53.00   81.80   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000 -120.0000 16

  6 omega   56.00   83.00   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -30.0000 15

  7 omega  -39.00   42.00   1.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000  -90.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0122902000
_diffrn_orient_matrix_UB_12      -0.0616011000
_diffrn_orient_matrix_UB_13      0.0006136000
_diffrn_orient_matrix_UB_21      0.0778065000
_diffrn_orient_matrix_UB_22      0.0044460000
_diffrn_orient_matrix_UB_23      0.0025305000
_diffrn_orient_matrix_UB_31      0.0143283000
_diffrn_orient_matrix_UB_32      0.0297479000
_diffrn_orient_matrix_UB_33      0.0650149000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            8354
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0573P)^2^+0.0099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1818
_reflns_number_gt                2049
_reflns_number_total             4553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00118h2.cif
_cod_data_source_block           liuxy1201
_cod_database_code               7116647
_reflns_odcompleteness_completeness 99.64
_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:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'