Stereoselective synthesis of oxa- and aza-angular triquinanes using tandem radical cyclization to vinylogous carbonates and carbamates.
Gharpure, Santosh J.; Niranjana, P.; Porwal, Suheel K.; Organic letters 14 (2012) 5476–5479; doi:10.1021/ol302557a

data_1508723
_publ_section_title
;
 Stereoselective synthesis of oxa- and aza-angular triquinanes using
 tandem radical cyclization to vinylogous carbonates and carbamates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5476
_journal_page_last               5479
_journal_paper_doi               10.1021/ol302557a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C23 H31 N O5 S'
_chemical_formula_weight         433.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.9960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4677(4)
_cell_length_b                   14.2273(4)
_cell_length_c                   13.5877(4)
_cell_measurement_reflns_used    7151
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      2.68
_cell_volume                     2213.86(12)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30796
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.14
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.8879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0755P)^2^+0.4183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                4448
_reflns_number_total             7152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302557a_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1508723