Double Reduction of Cyclic Aromatic Sulfonamides: Synthesis of (+)-Mesembrine and (+)-Mesembranol
Kimberly Geoghegan; Paul Evans; Journal of Organic Chemistry 78 (2013) 3410–3415; doi:10.1021/jo4000306

data_4028086
_publ_section_title
;
 Double Reduction of Cyclic Aromatic Sulfonamides: Synthesis of
 (+)-Mesembrine and (+)-Mesembranol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3410
_journal_page_last               3415
_journal_paper_doi               10.1021/jo4000306
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H24 Br N O4 S'
_chemical_formula_sum            'C18 H24 Br N O4 S'
_chemical_formula_weight         430.35
_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                 97.824(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4776(6)
_cell_length_b                   10.8233(7)
_cell_length_c                   19.093(2)
_cell_measurement_reflns_used    4580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.2863
_cell_measurement_theta_min      2.8544
_cell_volume                     1940.3(3)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15656
_diffrn_reflns_theta_full        23.34
_diffrn_reflns_theta_max         23.34
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.2522
_exptl_crystal_size_mid          0.2085
_exptl_crystal_size_min          0.0188
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0610P)^2^+1.5974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                4734
_reflns_number_total             5563
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo4000306_si_002.cif
_cod_data_source_block           eva57
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028086