Rhodium-catalyzed synthesis of substituted isoquinolones <i>via</i> a selective decarbonylation/alkyne insertion cascade of phthalimides.
Xu, Fen; Zhu, Wen-Jing; Wang, Juan; Ma, Qi; Shen, Li-Jing; Organic & biomolecular chemistry 18 (2020) 8219–8223; doi:10.1039/d0ob01793k

data_7157729
_publ_section_title
;
 Rhodium-catalyzed synthesis of substituted isoquinolones <i>via</i> a
 selective decarbonylation/alkyne insertion cascade of phthalimides.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8219
_journal_page_last               8223
_journal_paper_doi               10.1039/d0ob01793k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H22 N2 O'
_chemical_formula_sum            'C31 H22 N2 O'
_chemical_formula_weight         438.53
_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             2020-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-29 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                69.234(9)
_cell_angle_beta                 89.878(8)
_cell_angle_gamma                72.178(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6741(10)
_cell_length_b                   10.8198(12)
_cell_length_c                   12.5635(11)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    295.44(10)
_cell_measurement_theta_max      71.2290
_cell_measurement_theta_min      4.6450
_cell_volume                     1162.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      295.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_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    -72.00  25.00   1.00    3.85    --  -40.80  77.00-150.00   97
  2  \w   -108.00 -18.00   1.00    3.85    --  -40.80 -57.00 -60.00   90
  3  \w   -112.00 -83.00   1.00    3.85    --  -40.80 -57.00-180.00   29
  4  \w    -67.00  31.00   1.00    3.85    --  -40.80  57.00  90.00   98
  5  \w     52.00  77.00   1.00    3.85    --   40.80 -99.00-150.00   25
  6  \w     34.00  71.00   1.00   15.41    --  105.27 -61.00 -60.00   37
  7  \w     75.00 109.00   1.00   15.41    --  105.27 -95.00  30.00   34
  8  \w     73.00 109.00   1.00   15.41    --  105.27 -95.00 -60.00   36
  9  \w     23.00  62.00   1.00   15.41    --  105.27 -95.00  30.00   39
 10  \w     64.00 110.00   1.00   15.41    --  105.27-113.00-150.00   46
 11  \w    116.00 177.00   1.00   15.41    --  105.27  61.00-120.00   61
 12  \w     48.00  75.00   1.00   15.41    --  105.27 -45.00-180.00   27
 13  \w    109.00 176.00   1.00   15.41    --  105.27 125.00  30.00   67
 14  \w     33.00 129.00   1.00   15.41    --  105.27 -45.00  90.00   96
 15  \w    126.00 177.00   1.00   15.41    --  105.27  45.00  90.00   51
 16  \w     93.00 120.00   1.00   15.41    --  105.27  45.00  90.00   27
 17  \w     82.00 133.00   1.00   15.41    --  105.27 -61.00 -60.00   51
 18  \w     40.00  87.00   1.00   15.41    --  105.27 -77.00  90.00   47
 19  \w     40.00  68.00   1.00   15.41    --  105.27 -95.00 -60.00   28
 20  \w     47.00 172.00   1.00   15.41    --  105.27   0.00  60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1163084000
_diffrn_orient_matrix_UB_12      -0.1453532000
_diffrn_orient_matrix_UB_13      0.0315140000
_diffrn_orient_matrix_UB_21      0.0157417000
_diffrn_orient_matrix_UB_22      -0.0130582000
_diffrn_orient_matrix_UB_23      0.1258707000
_diffrn_orient_matrix_UB_31      -0.1208729000
_diffrn_orient_matrix_UB_32      -0.0682431000
_diffrn_orient_matrix_UB_33      0.0247127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7737
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.873
_diffrn_reflns_theta_min         3.790
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       prism
_exptl_crystal_F_000             458
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.237
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.1657
_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^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4066
_refine_ls_wR_factor_ref         0.4291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2955
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01793k2.cif
_cod_data_source_block           xf-20200802-13-2
_cod_depositor_comments
;
          Adding full bibliography for 7157729.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         174.60
_cod_original_formula_moiety         '0.4(C32 H22 N O)'
_cod_original_formula_units_Z            5
_cod_original_formula_sum        'C12.80 H8.80 N0.40 O0.40'
_cod_database_code               7157729
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.90
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              97947
_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 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.532