Synthesis of Indolo[2,1-a]isoquinoline Derivatives via Visible-light-induced Radical Cascade Cyclization Reactions
Wei, Yun-Long; Chen, Jian-Qiang; Sun, Bo; Xu, PengFei; Chemical Communications  (2019) –; doi:10.1039/C9CC02388G

data_7123332
_publ_section_title
;
 Synthesis of Indolo[2,1-a]isoquinoline Derivatives via
 Visible-light-induced Radical Cascade Cyclization Reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02388G
_journal_year                    2019
_chemical_formula_moiety         'C26 H21 N O2'
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.44
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.619(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7360(8)
_cell_length_b                   11.6168(7)
_cell_length_c                   11.8487(7)
_cell_measurement_reflns_used    3225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5770
_cell_measurement_theta_min      6.2970
_cell_volume                     1922.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -71.00  -38.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 22

  2 omega  -39.00  -12.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -120.0000 18

  3 omega  -61.00  -34.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 18

  4 omega  -85.00  -40.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 30

  5 omega   34.00  127.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -180.0000 62

  6 omega    2.00   87.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   30.0000 57

  7 omega   38.00  120.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 55

  8 omega   66.00   94.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 19

  9 omega   53.00   80.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 18

 10 omega   53.00   92.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 26

 11 omega   99.00  171.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 48

 12 omega   50.00  101.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 34

 13 omega   36.00   72.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 24

 14 omega   57.00  103.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 31

 15 omega   42.00   93.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 34

 16 omega   53.00   86.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 22

 17 omega   84.00  109.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 17

 18 omega  153.00  178.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 17

 19 omega  106.00  160.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0912526000
_diffrn_orient_matrix_UB_12      0.0688560000
_diffrn_orient_matrix_UB_13      -0.0081508000
_diffrn_orient_matrix_UB_21      -0.0368258000
_diffrn_orient_matrix_UB_22      -0.1012836000
_diffrn_orient_matrix_UB_23      0.0572567000
_diffrn_orient_matrix_UB_31      0.0499042000
_diffrn_orient_matrix_UB_32      0.0511072000
_diffrn_orient_matrix_UB_33      0.1243195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6677
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         5.48
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_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     264
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.3600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                2874
_reflns_number_total             3303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc02388g2.cif
_cod_data_source_block           weiyl_0719
_cod_original_cell_volume        1922.16(19)
_cod_database_code               7123332
_reflns_odcompleteness_completeness 96.96
_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.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2018-07-20
_olex2_submission_special_instructions 'No special instructions were received'