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_7123851
_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         '0.08(C34 H25 N2 O P Pd)'
_chemical_formula_sum            'C2.67 H1.96 N0.16 O0.08 P0.08 Pd0.08'
_chemical_formula_weight         48.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-20 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.007(2)
_cell_angle_gamma                90
_cell_formula_units_Z            51
_cell_length_a                   8.88834(18)
_cell_length_b                   18.6381(4)
_cell_length_c                   16.8048(3)
_cell_measurement_reflns_used    6510
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.4350
_cell_measurement_theta_min      5.0730
_cell_volume                     2723.01(10)
_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 1.000
_diffrn_measured_fraction_theta_max 0.975
_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    -50.00  31.00   1.00    1.59    --  -40.80  38.00  30.00   81
  2  \w     44.00  95.00   1.00    1.59    --   40.80-125.00  60.00   51
  3  \w     31.00  71.00   1.00    6.36    --  107.14 -77.00 120.00   40
  4  \w     38.00 117.00   1.00    6.36    --  107.14-125.00  90.00   79
  5  \w    103.00 134.00   1.00    6.36    --  107.14 -77.00 120.00   31
  6  \w    128.00 177.00   1.00    6.36    --  107.14  45.00 -60.00   49
  7  \w    126.00 177.00   1.00    6.36    --  107.14  45.00-150.00   51
  8  \w    117.00 168.00   1.00    6.36    --  107.14  45.00 -90.00   51
  9  \w     83.00 109.00   1.00    6.36    --  107.14  45.00-150.00   26
 10  \w     81.00 112.00   1.00    6.36    --  107.14  45.00 -90.00   31
 11  \w     83.00 109.00   1.00    6.36    --  107.14  45.00 -60.00   26
 12  \w     38.00 102.00   1.00    6.36    --  107.14 -95.00-180.00   64
 13  \w   -102.00 -75.00   1.00    1.59    --  -40.80-143.00 -55.00   27
 14  \w   -106.00 -17.00   1.00    1.59    --  -40.80 -57.00-120.00   89
;
_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      0.0181314000
_diffrn_orient_matrix_UB_12      -0.0723546000
_diffrn_orient_matrix_UB_13      0.0453737000
_diffrn_orient_matrix_UB_21      0.0129892000
_diffrn_orient_matrix_UB_22      0.0397325000
_diffrn_orient_matrix_UB_23      0.0815447000
_diffrn_orient_matrix_UB_31      -0.1757291000
_diffrn_orient_matrix_UB_32      -0.0045337000
_diffrn_orient_matrix_UB_33      -0.0089923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.503
_diffrn_reflns_theta_min         3.585
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43170
_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            red
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0361P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4789
_reflns_number_total             5342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04868e2.cif
_cod_data_source_block           sxj-s-504-tm1
_cod_original_cell_volume        2723.00(10)
_cod_database_code               7123851
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.314
_shelx_estimated_absorpt_t_min   0.292
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21),
  C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34)
;
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.592