Enantioselective bromocyclization of olefins catalyzed by chiral phosphoric acid.
Huang, Deshun; Wang, Haining; Xue, Fazhen; Guan, Huan; Li, Lijun; Peng, Xianyou; Shi, Yian; Organic letters 13 (2011) 6350–6353; doi:10.1021/ol202527g

data_1502570
_publ_section_title
;
 Enantioselective bromocyclization of olefins catalyzed by chiral
 phosphoric acid.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6350
_journal_page_last               6353
_journal_paper_doi               10.1021/ol202527g
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H36 Br N O2 S'
_chemical_formula_sum            'C22 H36 Br N O2 S'
_chemical_formula_weight         458.49
_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                 107.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8276(18)
_cell_length_b                   11.186(2)
_cell_length_c                   12.244(2)
_cell_measurement_reflns_used    4308
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4839
_cell_measurement_theta_min      1.7398
_cell_volume                     1155.8(4)
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13135
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.1448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                4997
_reflns_number_total             5278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202527g_si_001.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502570