Relay photocatalytic cascade reactions: synthesis of indolo[2,1-a]isoquinoline derivatives via double C(sp<sup>3</sup>)-H bond functionalization.
Cheng, Jian; Xie, Jin; Zhu, Chengjian; Chemical communications (Cambridge, England) 54 (2018) 1655–1658; doi:10.1039/c7cc09820k

data_7121179
_publ_section_title
;
 Relay photocatalytic cascade reactions: synthesis of
 indolo[2,1-a]isoquinoline derivatives via double C(sp<sup>3</sup>)-H bond
 functionalization.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1655
_journal_page_last               1658
_journal_paper_doi               10.1039/c7cc09820k
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C24 H23 N O4'
_chemical_formula_weight         389.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.143(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.593(10)
_cell_length_b                   8.000(8)
_cell_length_c                   13.517(14)
_cell_measurement_reflns_used    2608
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.55
_cell_volume                     1010.2(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5590
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.180
_exptl_absorpt_coefficient_mu    0.087
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_coef       0.037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0837P)^2^+0.0018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3003
_reflns_number_total             3437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09820k2.cif
_cod_data_source_block           20170222zcj_0m_a
_cod_depositor_comments          'Adding full bibliography for 7121179.cif.'
_cod_original_cell_volume        1010.3(18)
_cod_database_code               7121179
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              91678