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_4038429
_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_moiety         'C12 H12 Br N O2'
_chemical_formula_sum            'C12 H12 Br N O2'
_chemical_formula_weight         282.14
_chemical_name_systematic        LSN3179159
_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   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 112.7990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5606(6)
_cell_length_b                   8.3186(3)
_cell_length_c                   19.5153(7)
_cell_measurement_reflns_used    9449
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      78.15
_cell_measurement_theta_min      2.46
_cell_volume                     2328.74(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            84492
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         2.456
_exptl_absorpt_coefficient_mu    4.695
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.3794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       rods
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.988
_refine_diff_density_min         -1.512
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 3454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.116(5)
_refine_ls_extinction_coef       0.0078(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.641
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         8122
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.642
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0554
_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^)+(0.1000P)^2^+0.1373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                7897
_reflns_number_total             8122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00177_si_002.cif
_cod_data_source_block           compound_10
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038429
_elnb_number
;
EL19500-002
;
_lot_number
;
RP7-H81735-006
;
_comments
;
This is the second daset collected for this crystal at room temperature.
The data quality is good than the previous dataset 18013. 
The structure is solved with 0.0595 R factor and absolute stereochemistry
is determined.
;
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.138
_shelx_estimated_absorpt_t_max   0.651
_shelx_res_checksum              74898
_shelx_hkl_checksum              55883