Copper and palladium-catalyzed sequential reactions: one-pot synthesis of isoindolo[2,1-b]isoquinolin-7(5H)-ones.
Saini, Hitesh Kumar; Dhiman, Shiv; Nandwana, Nitesh Kumar; Krishnan, Rangan; Kumar, Anil; Organic & biomolecular chemistry 17 (2019) 4281–4290; doi:10.1039/c9ob00440h

data_7156744
_publ_section_title
;
 Copper and palladium-catalyzed sequential reactions: one-pot synthesis of
 isoindolo[2,1-b]isoquinolin-7(5H)-ones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4281
_journal_page_last               4290
_journal_paper_doi               10.1039/c9ob00440h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C30 H21 N O'
_chemical_formula_sum            'C30 H21 N O'
_chemical_formula_weight         411.48
_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             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-03 deposited with the CCDC.    2019-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.575(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9969(4)
_cell_length_b                   14.8584(3)
_cell_length_c                   10.6249(3)
_cell_measurement_reflns_used    5997
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      73.9090
_cell_measurement_theta_min      4.3690
_cell_volume                     2216.53(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_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    -23.00  81.00   0.50    7.00    --    0.00  57.00-180.00  208
  2  \w    -76.00 -50.00   0.50    7.00    --    0.00 -37.00 150.00   52
  3  \w      5.00  31.00   0.50    7.00    --    0.00  57.00 150.00   52
  4  \w    -44.00 -19.00   0.50    7.00    --    0.00 -37.00 150.00   50
  5  \w     52.00 128.00   0.50   28.00    --   95.80 -82.00 -30.00  152
  6  \w     80.00 142.00   0.50   28.00    --   95.80  30.00 -90.00  124
  7  \w     72.00 155.00   0.50   28.00    --   95.80  61.00 120.00  166
  8  \w     27.00  70.00   0.50   28.00    --   95.80 -61.00  30.00   86
  9  \w    108.00 169.00   0.50   28.00    --   95.80  45.00-180.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0863526000
_diffrn_orient_matrix_UB_12      0.0638768000
_diffrn_orient_matrix_UB_13      0.0457670000
_diffrn_orient_matrix_UB_21      -0.0658438000
_diffrn_orient_matrix_UB_22      0.0785451000
_diffrn_orient_matrix_UB_23      0.0046534000
_diffrn_orient_matrix_UB_31      0.0157892000
_diffrn_orient_matrix_UB_32      -0.0223066000
_diffrn_orient_matrix_UB_33      0.1479204000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.409
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00093(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0477P)^2^+0.7874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3723
_reflns_number_total             3961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00440h2.cif
_cod_data_source_block           exp-188-hks-934-2
_cod_depositor_comments
'Adding full bibliography for 7156743--7156745.cif.'
_cod_database_code               7156744
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 92.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C11(H11), C19(H19), C3(H3), C15(H15), C20(H20), C21(H21),
 C26(H26), C4(H4), C12(H12), C6(H6), C5(H5), C28(H28), C27(H27), C13(H13),
 C14(H14), C30(H30), C29(H29)
;
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.733