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_7123135
_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 rmad
_chemical_formula_moiety         'C38 H41 N3 O2 S'
_chemical_formula_sum            'C38 H41 N3 O2 S'
_chemical_formula_weight         603.80
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-22 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7314(4)
_cell_length_b                   11.3674(5)
_cell_length_c                   29.2938(12)
_cell_measurement_reflns_used    9306
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.653
_cell_measurement_theta_min      4.166
_cell_volume                     3240.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            35242
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.128
_diffrn_reflns_theta_min         4.165
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1540 before and 0.0909 after correction. The Ratio of minimum to maximum transmission is 0.7713. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.4288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5383
_reflns_number_total             6168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00412b2.cif
_cod_data_source_block           mjl18268_0m
_cod_database_code               7123135
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.928
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C21(H21A,H21B), C28(H28A,H28B), C29(H29A,
 H29B), C30(H30A,H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C33(H33), C34(H34), C36(H36), C37(H37)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              11115
_shelx_hkl_checksum              65877
_olex2_submission_special_instructions 'No special instructions were received'