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_7123855
_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         '0.06(C23 H16 N2 O2)'
_chemical_formula_sum            'C1.42 H0.98 N0.12 O0.12'
_chemical_formula_weight         21.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-10
_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                 103.63(2)
_cell_angle_gamma                90
_cell_formula_units_Z            65
_cell_length_a                   10.585(3)
_cell_length_b                   7.8514(18)
_cell_length_c                   21.381(4)
_cell_measurement_reflns_used    442
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      66.8020
_cell_measurement_theta_min      4.2810
_cell_volume                     1726.9(7)
_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 0.558
_diffrn_measured_fraction_theta_max 0.523
_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    -68.00   9.00   1.00   50.00    --  -40.80  57.00  60.00   77
  2  \w   -109.00 -82.00   1.00   50.00    --  -40.80-137.00 -18.00   27
  3  \w     49.00  96.00   1.00   50.00    --   40.80-125.00-120.00   47
  4  \w     52.00 128.00   1.00  215.00    --  107.14 -45.00  60.00   76
  5  \w     35.00  67.00   1.00  215.00    --  107.14-125.00 -60.00   32
;
_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      -0.0284235000
_diffrn_orient_matrix_UB_12      -0.1912120000
_diffrn_orient_matrix_UB_13      -0.0127428000
_diffrn_orient_matrix_UB_21      0.1202624000
_diffrn_orient_matrix_UB_22      -0.0446149000
_diffrn_orient_matrix_UB_23      0.0536532000
_diffrn_orient_matrix_UB_31      -0.0847285000
_diffrn_orient_matrix_UB_32      0.0003584000
_diffrn_orient_matrix_UB_33      0.0494570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.558
_diffrn_reflns_Laue_measured_fraction_max 0.523
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2339
_diffrn_reflns_point_group_measured_fraction_full 0.558
_diffrn_reflns_point_group_measured_fraction_max 0.523
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.381
_diffrn_reflns_theta_min         4.323
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25975
_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    1.355
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0828
_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^)+(0.1247P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2391
_refine_ls_wR_factor_ref         0.2789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1060
_reflns_number_total             1819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04868e2.cif
_cod_data_source_block           sxj-s-504-tm2
_cod_database_code               7123855
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 54.73
_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), C6(H6), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 2.864
_oxdiff_exptl_absorpt_empirical_full_min 0.605