Palladium-Catalyzed Decarbonylative Annulation of Phthalimides with Arynes: Direct Construction of Phenanthridinones
Meng, Yan-Yu; Si, Xiao-Ju; Song, Yuan-Yuan; Zhou, Hui-Min; Xu, Fen; Chemical Communications  (2019) –; doi:10.1039/C9CC04868E

data_7123854
_publ_section_title
;
 Palladium-Catalyzed Decarbonylative Annulation of Phthalimides with
 Arynes: Direct Construction of Phenanthridinones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04868E
_journal_year                    2019
_chemical_formula_moiety         '0.17(C23 H16 N2 O3)'
_chemical_formula_sum            'C3.83 H2.67 N0.33 O0.5'
_chemical_formula_weight         61.40
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                101.840(16)
_cell_angle_beta                 102.780(12)
_cell_angle_gamma                93.053(12)
_cell_formula_units_Z            12
_cell_length_a                   8.3599(9)
_cell_length_b                   9.1656(18)
_cell_length_c                   12.047(2)
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      71.8250
_cell_measurement_theta_min      3.8260
_cell_volume                     876.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.673
_diffrn_measured_fraction_theta_max 0.647
_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  36.00   1.00    2.50    --  -40.55  77.00   0.00  108
  2  \w     73.00 100.00   1.00    2.50    --   40.55  38.00  60.00   27
  3  \w     97.00 130.00   1.00   10.00    --  107.14 -30.00 120.00   33
  4  \w     53.00  81.00   1.00    2.50    --   40.55 -99.00  30.00   28
  5  \w     36.00 123.00   1.00   10.00    --  107.14 -61.00 -90.00   87
  6  \w     77.00 104.00   1.00   10.00    --  107.14 -95.00 -60.00   27
  7  \w     34.00 118.00   1.00   10.00    --  107.14-125.00-150.00   84
  8  \w     29.00  55.00   1.00   10.00    --  107.14 -95.00 -60.00   26
  9  \w     31.00 103.00   1.00   10.00    --  107.14 -95.00-120.00   72
 10  \w     54.00 154.00   1.00   10.00    --  107.14  15.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1338336000
_diffrn_orient_matrix_UB_12      0.0663025000
_diffrn_orient_matrix_UB_13      -0.0505709000
_diffrn_orient_matrix_UB_21      0.0059343000
_diffrn_orient_matrix_UB_22      -0.1557882000
_diffrn_orient_matrix_UB_23      -0.0761682000
_diffrn_orient_matrix_UB_31      -0.1347048000
_diffrn_orient_matrix_UB_32      0.0338433000
_diffrn_orient_matrix_UB_33      -0.0986575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.673
_diffrn_reflns_Laue_measured_fraction_max 0.647
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3074
_diffrn_reflns_point_group_measured_fraction_full 0.673
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.453
_diffrn_reflns_theta_min         3.859
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1106
_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^)+(0.1883P)^2^+1.8698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3692
_refine_ls_wR_factor_ref         0.3836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1775
_reflns_number_total             2281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04868e2.cif
_cod_data_source_block           sxj-20170520-s-45
_cod_original_cell_volume        876.4(3)
_cod_original_formula_sum        'C3.83 H2.67 N0.33 O0.50'
_cod_database_code               7123854
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     CHOcu
_shelx_estimated_absorpt_t_max   0.838
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 67.46
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C2(H2), C3(H3), C4(H4), C5(H5),
 C16(H16), C17(H17), C18(H18), C21(H21), C23(H23), C22(H22)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_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 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.615