EtOH-mediated cascade C(sp3)–H alkylation via aromatization-driven [1,6]-hydride transfer: green and divergent synthesis of spirocyclic azepino[4,3,2-cd]indoles
Shen, Yao-Bin; Zhuang, Qian-Hao; Wang, Xiao-Lin; An, Xiao-De; Qiu, Bin; Shi, Tiesheng; Xiao, Jian; Green Chemistry 26 (2024) 11899–11907; doi:10.1039/D4GC04534C

data_7249547
_publ_section_title
;
 EtOH-mediated cascade C(sp3)--H alkylation via aromatization-driven
 [1,6]-hydride transfer: green and divergent synthesis of spirocyclic
 azepino[4,3,2-cd]indoles
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              11899
_journal_page_last               11907
_journal_paper_doi               10.1039/D4GC04534C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C29 H24 N4 O6 S'
_chemical_formula_weight         556.58
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-10-11 deposited with the CCDC.	2024-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.431(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7872(6)
_cell_length_b                   14.4008(7)
_cell_length_c                   15.0129(7)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.22
_cell_volume                     2573.4(2)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker PHTON II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46259
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.031
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5894
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.0100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3576
_reflns_number_total             5894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc04534c2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7249547--7249550.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249547
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              85225
_shelx_hkl_checksum              2620