cis-Selective synthesis of 1,3-disubstituted tetrahydro-β-carbolines from N-sulfonyl N,S-acetals.
Luo, Shao-Xiong; Liu, Yanzhou; Lambrecht, Michael J.; Ortwine, Daniel F.; DiPasquale, Antonio G.; Liang, Jun; Wang, Xiaojing; Zbieg, Jason R.; Li, Jun; Organic & biomolecular chemistry 17 (2019) 9510–; doi:10.1039/c9ob01796h

data_7157147
_publ_section_title
;
 cis-Selective synthesis of 1,3-disubstituted tetrahydro-\b-carbolines
 from N-sulfonyl N,S-acetals.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9510
_journal_paper_doi               10.1039/c9ob01796h
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H24 N2 O2 S'
_chemical_formula_weight         416.52
_chemical_name_systematic        28
_space_group.centring_type       primitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-04 deposited with the CCDC.    2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0518(4)
_cell_length_b                   12.1315(5)
_cell_length_c                   18.9731(8)
_cell_measurement_reflns_used    8729
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.49
_cell_volume                     2083.47(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_refln_scan_rate          20
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.377
_diffrn_reflns_theta_min         1.993
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.7032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3452
_reflns_number_total             3817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01796h2.cif
_cod_data_source_block           28
_cod_depositor_comments
'Adding full bibliography for 7157147--7157148.cif.'
_cod_database_code               7157147
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              59813