Rh(III)-Catalyzed Oxidative Annulation of Isoquinolones with Diazoketoesters Featuring an in Situ Deacylation: Synthesis of Isoindoloisoquinolones and Their Transformation to Rosettacin Analogues.
Guo, Shenghai; Sun, Lincong; Wang, Fang; Zhang, Xinying; Fan, Xuesen; The Journal of organic chemistry 83 (2018) 12034–12043; doi:10.1021/acs.joc.8b01982

data_4035278
_publ_section_title
;
 Rh(III)-Catalyzed Oxidative Annulation of Isoquinolones with
 Diazoketoesters Featuring an in Situ Deacylation: Synthesis of
 Isoindoloisoquinolones and Their Transformation to Rosettacin Analogues.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12034
_journal_page_last               12043
_journal_paper_doi               10.1021/acs.joc.8b01982
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H17 N O3'
_chemical_formula_sum            'C24 H17 N O3'
_chemical_formula_weight         367.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-28
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                81.279(2)
_cell_angle_beta                 84.444(2)
_cell_angle_gamma                84.681(2)
_cell_formula_units_Z            2
_cell_length_a                   5.97007(13)
_cell_length_b                   10.7499(3)
_cell_length_c                   14.3987(4)
_cell_measurement_reflns_used    8595
_cell_measurement_temperature    295.99(10)
_cell_measurement_theta_max      72.3010
_cell_measurement_theta_min      5.5400
_cell_volume                     906.24(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -55.00  33.00   1.00    1.00    --  -36.21  38.00 120.00   88
  2  \w      1.00  75.00   1.00    1.00    --   36.21 -99.00  60.00   74
  3  \w      1.00  75.00   1.00    1.00    --   36.21 -99.00 -90.00   74
  4  \w      7.00 108.00   1.00    1.00    --   36.21  19.00  90.00  101
  5  \w    -31.00  53.00   1.00    1.00    --   36.21 -57.00-120.00   84
  6  \w     23.00  90.00   1.00    1.00    --   36.21-125.00-120.00   67
  7  \w      1.00  75.00   1.00    1.00    --   36.21 -99.00-120.00   74
  8  \w     23.00  90.00   1.00    1.00    --   36.21-125.00 -30.00   67
  9  \w    -31.00  53.00   1.00    1.00    --   36.21 -57.00 -30.00   84
 10  \w    -16.00  67.00   1.00    1.00    --   36.21 -84.00 179.00   83
 11  \w      7.00 108.00   1.00    1.00    --   36.21  19.00-180.00  101
 12  \w      1.00  75.00   1.00    1.00    --   36.21 -99.00-150.00   74
 13  \w      1.00  75.00   1.00    1.00    --   36.21 -99.00 150.00   74
 14  \w    100.00 178.00   1.00    1.00    --  109.31 111.00  60.00   78
 15  \w     39.00 116.00   1.00    1.00    --  109.31-111.00  30.00   77
 16  \w     91.00 176.00   1.00    1.00    --  109.31  61.00 -60.00   85
 17  \w     39.00 116.00   1.00    1.00    --  109.31-111.00-120.00   77
 18  \w     40.00 109.00   1.00    1.00    --  109.31 -95.00   0.00   69
 19  \w     42.00 127.00   1.00    1.00    --  109.31 -61.00  60.00   85
 20  \w     42.00 127.00   1.00    1.00    --  109.31 -61.00-120.00   85
 21  \w     39.00 131.00   1.00    1.00    --  109.31 -30.00  90.00   92
 22  \w     41.00 127.00   1.00    1.00    --  109.31 -45.00 -30.00   86
 23  \w     39.00 116.00   1.00    1.00    --  109.31-111.00 120.00   77
 24  \w     41.00 127.00   1.00    1.00    --  109.31 -45.00-180.00   86
 25  \w     92.00 178.00   1.00    1.00    --  109.31  45.00 120.00   86
 26  \w     40.00 109.00   1.00    1.00    --  109.31 -95.00-120.00   69
 27  \w     71.00 178.00   1.00    1.00    --  109.31  15.00  60.00  107
 28  \w   -105.00 -17.00   1.00    1.00    --  -36.21 -38.00 -60.00   88
 29  \w      9.00 104.00   1.00    1.00    --   36.21  77.00  30.00   95
 30  \w     19.00 103.00   1.00    1.00    --   36.21  57.00  30.00   84
 31  \w    -33.00  51.00   1.00    1.00    --   36.21   0.00 -30.00   84
 32  \w      9.00 104.00   1.00    1.00    --   36.21  77.00-120.00   95
 33  \w    -35.00  66.00   1.00    1.00    --   36.21 -19.00 -60.00  101
 34  \w      9.00 104.00   1.00    1.00    --   36.21  77.00 120.00   95
 35  \w      9.00 104.00   1.00    1.00    --   36.21  77.00   0.00   95
 36  \w      9.00 104.00   1.00    1.00    --   36.21  77.00-150.00   95
 37  \w      9.00 104.00   1.00    1.00    --   36.21  77.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0655517000
_diffrn_orient_matrix_UB_12      -0.1078600000
_diffrn_orient_matrix_UB_13      -0.0487092000
_diffrn_orient_matrix_UB_21      -0.0806655000
_diffrn_orient_matrix_UB_22      0.0971183000
_diffrn_orient_matrix_UB_23      -0.0824632000
_diffrn_orient_matrix_UB_31      0.2384121000
_diffrn_orient_matrix_UB_32      -0.0093807000
_diffrn_orient_matrix_UB_33      -0.0512597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11342
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.511
_diffrn_reflns_theta_min         4.174
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.1951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3256
_reflns_number_total             3514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01982_si_002.cif
_cod_data_source_block           slc-98-1
_cod_database_code               4035278
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.111
_oxdiff_exptl_absorpt_empirical_full_min 0.521