Synthesis of Azepinoindoles via Rhodium-Catalyzed Formal Aza-[4 + 3] Cycloaddition Reaction of 3-Diazoindolin-2-imines with 1,3-Dienes in One-Pot.
Kim, Sanghyuck; Kim, Hyunseok; Um, Kyusik; Lee, Phil Ho; The Journal of organic chemistry 82 (2017) 9808–9815; doi:10.1021/acs.joc.7b01150

data_4033061
_publ_section_title
;
 Synthesis of Azepinoindoles via Rhodium-Catalyzed Formal Aza-[4 + 3]
 Cycloaddition Reaction of 3-Diazoindolin-2-imines with 1,3-Dienes in
 One-Pot.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9808
_journal_page_last               9815
_journal_paper_doi               10.1021/acs.joc.7b01150
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C26 H23 Br N2 O2 S'
_chemical_formula_weight         507.43
_chemical_name_common            KSH-2733
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                94.023(3)
_cell_angle_beta                 94.343(3)
_cell_angle_gamma                95.709(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2539(6)
_cell_length_b                   9.3035(6)
_cell_length_c                   15.4181(10)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.5635
_cell_measurement_theta_min      2.6579
_cell_volume                     1171.10(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21409
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    1.870
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.725
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.861
_refine_ls_R_factor_all          0.1653
_refine_ls_R_factor_gt           0.1524
_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^)+(0.1000P)^2^+49.0698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3515
_refine_ls_wR_factor_ref         0.3597
_reflns_number_gt                3366
_reflns_number_total             3789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01150_si_002.cif
_cod_data_source_block           I
_cod_database_code               4033061