Rhodium-catalyzed asymmetric formal cycloadditions of racemic butadiene monoxide with imines.
Liu, Zhaoqun; Feng, Xiangqing; Du, Haifeng; Organic letters 14 (2012) 3154–3157; doi:10.1021/ol301248d

data_1507835
_publ_section_title
;
 Rhodium-catalyzed asymmetric formal cycloadditions of racemic butadiene
 monoxide with imines.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3154
_journal_page_last               3157
_journal_paper_doi               10.1021/ol301248d
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 Br N2 O3'
_chemical_formula_sum            'C19 H17 Br N2 O3'
_chemical_formula_weight         401.26
_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                 97.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   10.975(2)
_cell_length_b                   20.829(4)
_cell_length_c                   11.516(2)
_cell_measurement_reflns_used    8552
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      1.8731
_cell_volume                     2607.9(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29307
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     699
_refine_ls_number_reflns         11858
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                10705
_reflns_number_total             11858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301248d_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 1507835.cif.'
_cod_original_cell_volume        2607.9(9)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507835