Diastereoselective Pictet-Spengler Based Synthesis of a Chiral Tetrahydroisoquinoline D1 Potentiator.
Magnus, Nicholas Andrew; Buser, Jonas Y.; Embry, Matthew C.; Kallman, Neil John; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00177

data_4038428
_publ_section_title
;
 Diastereoselective Pictet-Spengler Based Synthesis of a Chiral
 Tetrahydroisoquinoline D1 Potentiator.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00177
_journal_year                    2020
_chemical_formula_sum            'C18 H18 Br N O4 S'
_chemical_formula_weight         424.30
_chemical_name_systematic        LSN3495203
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.348(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5479(16)
_cell_length_b                   5.7655(9)
_cell_length_c                   14.537(2)
_cell_measurement_reflns_used    8561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      3.24
_cell_volume                     907.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX3 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.467
_diffrn_reflns_theta_min         3.242
_exptl_absorpt_coefficient_mu    4.361
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.5396
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.259
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0784
_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^)+(0.1583P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2253
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                3067
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00177_si_001.cif
_cod_data_source_block           compound_8
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038428
_elnb_number
;
RP7-H81584-086
;
_lot_number
;
RP7-H80584-086
;
_comments
;

;
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.561
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              46239
_shelx_hkl_checksum              14888