Enantioselective Bromocyclization of Tryptamines Induced by Chiral Co(III)-Complex-Templated Brønsted Acids under an Air Atmosphere.
Liu, Kun; Jiang, Hua-Jie; Li, Na; Li, Hui; Wang, Jing; Zhang, Zheng-Zhu; Yu, Jie; The Journal of organic chemistry 83 (2018) 6815–6823; doi:10.1021/acs.joc.8b01196

data_4035802
_publ_section_title
;
 Enantioselective Bromocyclization of Tryptamines Induced by Chiral
 Co(III)-Complex-Templated Br\/onsted Acids under an Air Atmosphere.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6815
_journal_page_last               6823
_journal_paper_doi               10.1021/acs.joc.8b01196
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H27 Br N2 O4'
_chemical_formula_weight         439.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.93050(10)
_cell_length_b                   12.05900(10)
_cell_length_c                   18.5891(2)
_cell_measurement_reflns_used    6061
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      71.1880
_cell_measurement_theta_min      3.6760
_cell_volume                     2226.08(4)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7769
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.298
_diffrn_reflns_theta_min         4.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.006(8)
_refine_ls_extinction_coef       0.0026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0382P)^2^+0.4856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                4074
_reflns_number_total             4198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01196_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4035802
_shelx_estimated_absorpt_t_min   0.516
_shelx_estimated_absorpt_t_max   0.612
_shelxl_version_number           2013-4
_shelx_res_checksum              73961
_shelx_hkl_checksum              9928