Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels-Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents.
Attaba, Nassilia; Taylor, James E.; Slawin, Alexandra M. Z.; Smith, Andrew D.; The Journal of organic chemistry 80 (2015) 9728–9739; doi:10.1021/acs.joc.5b01820

data_4036401
_publ_section_title
;
 Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels-Alder Reactions
 Using \a,\b-Unsaturated Trichloromethyl Ketones as Amide Equivalents.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9728
_journal_page_last               9739
_journal_paper_doi               10.1021/acs.joc.5b01820
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27.5 H30.5 Cl1.5 N2 O3'
_chemical_formula_sum            'C27.5 H30.5 Cl1.5 N2 O3'
_chemical_formula_weight         490.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-06
_audit_creation_method           'by CrystalStructure 4.1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   9.960(2)
_cell_length_b                   18.650(4)
_cell_length_c                   28.449(5)
_cell_measurement_reflns_used    3587
_cell_measurement_temperature    125
_cell_measurement_theta_max      74.00
_cell_measurement_theta_min      24.00
_cell_volume                     5284.5(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            57874
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         67.926
_diffrn_reflns_theta_min         2.833
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2072.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.79
_refine_ls_abs_structure_details
;
 Flack x determined using 3530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T. Acta Cryst. B69 (2013) 249-259).

;
_refine_ls_abs_structure_Flack   0.031(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     633
_refine_ls_number_reflns         9569
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0741
_refine_ls_shift/su_max          0.053
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1392P)^2^+2.6395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2120
_reflns_number_gt                8740
_reflns_number_total             9569
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5b01820_si_002.cif
_cod_data_source_block           28
_cod_database_code               4036401
_shelx_res_checksum              61371
_shelx_hkl_checksum              75771