Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes.
Fang, Li-Chao; Hsung, Richard P.; Organic letters 16 (2014) 1826–1829; doi:10.1021/ol500390a

data_1513945
_publ_section_title
;
 Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2]
 Cycloaddition of Chiral Cyclic 2-Amidodienes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1826
_journal_page_last               1829
_journal_paper_doi               10.1021/ol500390a
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration adrm
_chemical_formula_moiety         'C27 H32 N2 O4 S'
_chemical_formula_sum            'C27 H32 N2 O4 S'
_chemical_formula_weight         480.60
_chemical_name_common            13315a
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5295(6)
_cell_length_b                   16.1868(15)
_cell_length_c                   22.781(2)
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.65
_cell_measurement_theta_min      3.88
_cell_volume                     2407.8(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-AXS D8 Photon-100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20427
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.271
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'Cu ImuS Micro-focus'
_exptl_absorpt_coefficient_mu    1.492
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6298
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.034(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.3887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4087
_reflns_number_total             4326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500390a_si_003.cif
_cod_data_source_block           13315a
_cod_database_code               1513945
_shelx_estimated_absorpt_t_min   0.707
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2013-3
_shelx_res_checksum              42473
_shelx_hkl_checksum              31056