A Highly Stereoselective Diels–Alder Cycloaddition of Enones with Chiral Cyclic 2-Amidodienes Derived from Allenamides
Fang, Li-Chao; Hsung, Richard P.; Ma, Zhi-Xiong; Presser, William R.; Organic Letters 15 (2013) 4842–; doi:10.1021/ol402254p

data_1512346
_publ_section_title
;
 A Highly Stereoselective Diels--Alder Cycloaddition of Enones with Chiral
 Cyclic 2-Amidodienes Derived from Allenamides
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4842
_journal_paper_doi               10.1021/ol402254p
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H24 Br N O3'
_chemical_formula_sum            'C21 H24 Br N O3'
_chemical_formula_weight         418.32
_chemical_name_common            13100a
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.972(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4311(2)
_cell_length_b                   10.2155(3)
_cell_length_c                   14.4708(5)
_cell_measurement_reflns_used    2912
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      5.30
_cell_volume                     950.55(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Photon-100'
_diffrn_radiation_monochromator  'normal parabolic mirrors'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10349
_diffrn_reflns_theta_full        68.30
_diffrn_reflns_theta_max         68.30
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  0.7259
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.023(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+0.2050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0490
_reflns_number_gt                3428
_reflns_number_total             3433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402254p_si_003.cif
_cod_data_source_block           13100a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1512346