Synthetic Studies toward Halichlorine: Complex Azaspirocycle Formation with Use of an NBS-Promoted Semipinacol Reaction
Paul B. Hurley; Gregory R. Dake; Journal of Organic Chemistry 73 (2008) 4131–4138; doi:10.1021/jo800336k

data_4023444
_publ_section_title
;
 Synthetic Studies toward Halichlorine: Complex Azaspirocycle Formation
 with Use of an NBS-Promoted Semipinacol Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4131
_journal_page_last               4138
_journal_paper_doi               10.1021/jo800336k
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C31 H42 Br N O5 S'
_chemical_formula_weight         620.63
_chemical_name_systematic
;
 ?
;
_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                 111.993(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8742(16)
_cell_length_b                   7.6796(9)
_cell_length_c                   15.1970(15)
_cell_measurement_reflns_used    8974
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.72
_cell_volume                     1501.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33368
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.027(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         7137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                5915
_reflns_number_total             7137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800336k-File001.cif
_cod_data_source_block           gd016
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023444