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_4033475
_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            'C22 H22 N4 O5'
_chemical_formula_weight         422.43
_chemical_name_common            MCY-328
_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   mixed
_cell_angle_alpha                82.5800(11)
_cell_angle_beta                 89.9930(12)
_cell_angle_gamma                73.8609(12)
_cell_formula_units_Z            2
_cell_length_a                   7.0232(9)
_cell_length_b                   8.8151(11)
_cell_length_c                   17.845(2)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.2862
_cell_measurement_theta_min      2.8234
_cell_volume                     1051.6(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24651
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0427P)^2^+0.3906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3169
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00115_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4033474--4033476.cif.'
_cod_database_code               4033475