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_7156743
_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         'C22 H16 Br N O'
_chemical_formula_sum            'C22 H16 Br N O'
_chemical_formula_weight         390.27
_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             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                89.931(4)
_cell_angle_beta                 69.876(5)
_cell_angle_gamma                83.515(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7437(4)
_cell_length_b                   9.0981(5)
_cell_length_c                   11.3532(6)
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.6280
_cell_measurement_theta_min      3.5170
_cell_volume                     841.91(8)
_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 0.996
_diffrn_measured_fraction_theta_max 0.867
_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      3.00  54.00   0.50   32.11    --    0.00  37.00  90.00  102
  2  \w     12.00  89.00   0.50   32.11    --    0.00  77.00 -30.00  154
  3  \w    -66.00  30.00   0.50   32.11    --    0.00 -77.00 -30.00  192
  4  \w    -15.00  86.00   0.50   32.11    --    0.00  77.00 -90.00  202
  5  \w    -42.00  22.00   0.50   32.11    --    0.00 -19.00  90.00  128
;
_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      -0.0583071000
_diffrn_orient_matrix_UB_12      0.0558021000
_diffrn_orient_matrix_UB_13      -0.0086387000
_diffrn_orient_matrix_UB_21      -0.0555221000
_diffrn_orient_matrix_UB_22      -0.0117390000
_diffrn_orient_matrix_UB_23      0.0606816000
_diffrn_orient_matrix_UB_31      0.0330226000
_diffrn_orient_matrix_UB_32      0.0539896000
_diffrn_orient_matrix_UB_33      0.0260316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12080
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.907
_diffrn_reflns_theta_min         3.562
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87862
_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            Colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       Block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3158
_reflns_number_total             4229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00440h2.cif
_cod_data_source_block           exp_189-hks-934-1
_cod_depositor_comments
'Adding full bibliography for 7156743--7156745.cif.'
_cod_database_code               7156743
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3), C18(H18), C4(H4), C9(H9), C11(H11), C12(H12), C15(H15), C21(H21),
 C19(H19), C5(H5), C13(H13), C20(H20), C14(H14), C6(H6)
;
_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.846