Enantioselective Synthesis of Yohimbine Analogues by an Organocatalytic and Pot-Economic Strategy.
Kao, Hsin-Kai; Lin, Xin-Jie; Hong, Bor-Cherng; Yang, Van-Wei; Lee, Gene-Hsiang; The Journal of organic chemistry 84 (2019) 12138–12147; doi:10.1021/acs.joc.9b01193

data_4034449
_publ_section_title
;
 Enantioselective Synthesis of Yohimbine Analogues by an Organocatalytic
 and Pot-Economic Strategy.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12138
_journal_page_last               12147
_journal_paper_doi               10.1021/acs.joc.9b01193
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H26 Br N3 O2'
_chemical_formula_weight         480.40
_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                 98.2257(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6471(2)
_cell_length_b                   14.5583(4)
_cell_length_c                   13.5116(4)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.02
_cell_measurement_theta_min      3.04
_cell_volume                     1099.39(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6357
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.988
_diffrn_reflns_theta_min         3.305
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.5490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 2039 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.042(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                4374
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01193_si_003.cif
_cod_data_source_block           ic19512
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034449
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.398
_shelx_estimated_absorpt_t_max   0.779
_shelx_res_checksum              27457
_shelx_hkl_checksum              78573