Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives.
Zhu, Min; Zheng, Chao; Zhang, Xiao; You, Shu-Li; Journal of the American Chemical Society 141 (2019) 2636–2644; doi:10.1021/jacs.8b12965

data_4128163
_publ_section_title
;
 Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via
 Visible-Light-Promoted Intramolecular Dearomatization of Indole
 Derivatives.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2636
_journal_page_last               2644
_journal_paper_doi               10.1021/jacs.8b12965
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C25 H22 F3 N O5'
_chemical_formula_weight         473.43
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.2580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5048(3)
_cell_length_b                   19.9335(6)
_cell_length_c                   12.2973(4)
_cell_measurement_reflns_used    4798
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.720
_cell_measurement_theta_min      6.008
_cell_volume                     2267.80(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12493
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.004
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+1.0326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3352
_reflns_number_total             4408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12965_si_002.cif
_cod_data_source_block           mo_d8v18678_0m
_cod_database_code               4128163
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
_shelx_res_checksum              85092
_shelx_hkl_checksum              26281