Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones
Gerri E. Hutson; Yunus E. Türkmen; Viresh H. Rawal; Journal of the American Chemical Society 135 (2013) 4988–4991; doi:10.1021/ja401908m

data_4119550
_publ_section_title
;
 Salen Promoted Enantioselective Nazarov Cyclizations of Activated and
 Unactivated Dienones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4988
_journal_page_last               4991
_journal_paper_doi               10.1021/ja401908m
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H20 Br2 O'
_chemical_formula_weight         400.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                 110.196(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.254(11)
_cell_length_b                   6.962(8)
_cell_length_c                   11.580(13)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      1.87
_cell_volume                     775.9(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.1399
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6969
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    5.218
_exptl_absorpt_correction_T_max  0.4218
_exptl_absorpt_correction_T_min  0.1885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
absorption corrections were made based on correspondance of
equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker 
Analytical x-ray Systems, Madison, WI)
;
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0891
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1369P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2237
_reflns_number_gt                1729
_reflns_number_total             2725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401908m_si_002.cif
_cod_data_source_block           turk14s
_cod_database_code               4119550