Silver-Catalyzed Decarboxylative Radical Cascade Cyclization toward Benzimidazo[2,1-a]isoquinolin-6(5H)-ones
Sun, Kai; Li, Shi-Jun; Chen, Xiaolan; Liu, Yan; Huang, Xianqiang; Wei, Donghui; Qu, Lingbo; Zhao, Yufen; Yu, Bing; Chemical Communications  (2019) –; doi:10.1039/C8CC10243K

data_7122930
_publ_section_title
;
 Silver-Catalyzed Decarboxylative Radical Cascade Cyclization toward
 Benzimidazo[2,1-a]isoquinolin-6(5H)-ones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC10243K
_journal_year                    2019
_chemical_formula_moiety         'C21 H22 N2 O'
_chemical_formula_sum            'C21 H22 N2 O'
_chemical_formula_weight         318.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-09-26 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.5024(4)
_cell_length_b                   11.1420(2)
_cell_length_c                   19.3013(5)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8380
_cell_measurement_theta_min      4.5640
_cell_volume                     3548.93(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega    0.00   35.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000    0.0000 35

  2 omega    2.00   30.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -90.0000 28

  3 omega  -63.00  -33.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 30

  4 omega  -52.00  -23.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000    0.0000 29

  5 omega  -31.00    9.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 40

  6 omega   14.00   51.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 37

  7 omega   23.00   50.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 27

  8 omega   24.00   49.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 25

  9 omega   61.00  108.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 47

 10 omega   74.00  106.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 32

 11 omega    8.00   53.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 45

 12 omega   80.00  110.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 30

 13 omega   75.00  100.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 25

 14 omega   63.00   91.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 28

 15 omega   39.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 52

 16 omega   39.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 28

 17 omega   48.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 39

 18 omega   38.00   70.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 32

 19 omega  108.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 66

 20 omega   39.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 76

 21 omega  103.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 47

 22 omega   61.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 26

 23 omega   51.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 36

 24 omega   92.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 75

 25 omega   39.00   70.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0637094000
_diffrn_orient_matrix_UB_12      0.0034828000
_diffrn_orient_matrix_UB_13      -0.0581564000
_diffrn_orient_matrix_UB_21      -0.0670289000
_diffrn_orient_matrix_UB_22      -0.0225910000
_diffrn_orient_matrix_UB_23      -0.0540574000
_diffrn_orient_matrix_UB_31      -0.0127589000
_diffrn_orient_matrix_UB_32      0.1363811000
_diffrn_orient_matrix_UB_33      -0.0074637000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13149
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.734
_diffrn_reflns_theta_min         4.582
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0804P)^2^+0.3573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2551
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc10243k2.cif
_cod_data_source_block           20170328
_cod_database_code               7122930
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C19H12O4
_reflns_odcompleteness_completeness 99.80
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'