Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines.
Baek, Yonghyeon; Maeng, Chanyoung; Kim, Hyunseok; Lee, Phil Ho; The Journal of organic chemistry 83 (2018) 2349–2360; doi:10.1021/acs.joc.8b00115

data_4033476
_publ_section_title
;
 Regioselective Synthesis of Indolopyrazines through a Sequential
 Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction
 of Diazoindolinimines with Azirines.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2349
_journal_page_last               2360
_journal_paper_doi               10.1021/acs.joc.8b00115
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C23 H16 Br N3'
_chemical_formula_weight         414.30
_chemical_name_common            MCY-589
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 107.4410(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1674(2)
_cell_length_b                   15.1172(4)
_cell_length_c                   12.4673(3)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.0736
_cell_measurement_theta_min      2.1786
_cell_volume                     1828.16(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0606
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            63475
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.261
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.932
_refine_diff_density_min         -1.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0351P)^2^+1.8486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                3516
_reflns_number_total             4645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00115_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4033474--4033476.cif.'
_cod_database_code               4033476