Enantioselective synthesis of 4,5,6,7-tetrahydroindoles via olefin cross-metathesis/intramolecular Friedel–Crafts alkylation reaction of pyrroles
Zhang, Jun-Wei; Liu, Xiao-Wei; Gu, Qing; Shi, Xiao-Xin; You, Shu-Li; Organic Chemistry Frontiers 2 (2015) 476–; doi:10.1039/C5QO00034C

data_1553106
_publ_section_title
;
 Enantioselective synthesis of 4,5,6,7-tetrahydroindoles via olefin
 cross-metathesis/intramolecular Friedel--Crafts alkylation reaction of
 pyrroles
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              476
_journal_paper_doi               10.1039/C5QO00034C
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H30 Br N O5'
_chemical_formula_weight         600.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           23
_space_group_name_Hall           'I 2 2'
_space_group_name_H-M_alt        'I 2 2 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-27 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.713(12)
_cell_length_b                   28.08(2)
_cell_length_c                   28.507(18)
_cell_measurement_reflns_used    2903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.130
_cell_measurement_theta_min      4.525
_cell_volume                     12578(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.1209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.018
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             4960
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.103
_platon_squeeze_details
;
;
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
; 
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.031(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         11716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0686
_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^)+(0.0842P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5778
_reflns_number_total             11716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00034c2.cif
_cod_data_source_block           cd214165
_cod_database_code               1553106
_shelxl_version_number           2013-4
_shelx_res_checksum              66765
_shelx_hkl_checksum              40907