Gold(I)-Catalyzed Enantioselective Synthesis of Polycyclic Indoline Skeletons and Enantiomerically Enriched β-Substituted Tryptamine-Allenes by Kinetic Resolution
Shi, Min; Zhang, Yan-Yan; Wei, Yin; Chemical Communications  (2019) –; doi:10.1039/C9CC00412B

data_7123134
_publ_section_title
;
 Gold(I)-Catalyzed Enantioselective Synthesis of Polycyclic Indoline
 Skeletons and Enantiomerically Enriched \b-Substituted Tryptamine-Allenes
 by Kinetic Resolution
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00412B
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C28 H26 Cl2 N2 O2 S'
_chemical_formula_weight         525.47
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-05-31 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.969(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5142(5)
_cell_length_b                   11.8312(8)
_cell_length_c                   13.0004(8)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      109.917
_cell_measurement_theta_min      8.979
_cell_volume                     1252.56(14)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12896
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.094
_diffrn_reflns_theta_min         4.488
_exptl_absorpt_coefficient_mu    2.210
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         2.092
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
; 
 Flack x determined using 1664 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.199(11)
_refine_ls_extinction_coef       0.064(9)
_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   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0862
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2492
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                4109
_reflns_number_total             4533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00412b2.cif
_cod_data_source_block           mjr18225_0m
_cod_database_code               7123134
_shelx_estimated_absorpt_t_min   0.719
_shelx_estimated_absorpt_t_max   0.843
_shelxl_version_number           2013-4
_shelx_res_checksum              7306
_shelx_hkl_checksum              34321