Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (N-Sulfinyl Imines)
Franklin A. Davis; Narendra V. Gaddiraju; Naresh Theddu; Joshua R. Hummel; Sandeep K. Kondaveeti; Michael J. Zdilla; Journal of Organic Chemistry 77 (2012) 2345–2359; doi:10.1021/jo202652f

data_4027042
_publ_section_title
;
 Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines
 (N-Sulfinyl Imines)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2345
_journal_page_last               2359
_journal_paper_doi               10.1021/jo202652f
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H21 N O5'
_chemical_formula_sum            'C15 H21 N O5'
_chemical_formula_weight         295.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2502(11)
_cell_length_b                   22.633(2)
_cell_length_c                   5.7548(5)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      86.059
_cell_measurement_theta_min      4.389
_cell_volume                     1465.3(2)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'COSMO (Bruker-AXS)'
_computing_data_reduction        'SADBAS (Bruker-AXS)'
_computing_molecular_graphics    'XP (Sheldrick 2008)'
_computing_publication_material  'APEX2 Report Generator (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Kappa APEX II DUO'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2503
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.8644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

6949 Corrected reflections written to file
 Estimated minimum and maximum transmission:  0.6278  0.7528
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       neddle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
diffuse electron density was removed with squeeze giving 48 electron 
most likely to be 3 water molecules (44)
;
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2196
_reflns_number_total             2503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202652f_si_001.cif
_cod_data_source_block           sandeep_sqz
_cod_database_code               4027042