Cascade Synthesis of 3-Functionalized Indoles from Nitrones and their Conversion to Cycloheptanone-Fused Indoles.
Kroc, Michelle A.; Prajapati, Ami; Wink, Donald J.; Anderson, Laura L.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02638

data_4033206
_publ_section_title
;
 Cascade Synthesis of 3-Functionalized Indoles from Nitrones and their
 Conversion to Cycloheptanone-Fused Indoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02638
_journal_year                    2017
_chemical_formula_moiety         'C26 H22 Br N O3'
_chemical_formula_sum            'C26 H22 Br N O3'
_chemical_formula_weight         476.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.262(4)
_cell_angle_beta                 97.066(4)
_cell_angle_gamma                100.438(4)
_cell_formula_units_Z            2
_cell_length_a                   8.959(2)
_cell_length_b                   10.712(3)
_cell_length_c                   11.971(3)
_cell_measurement_reflns_used    2851
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.0208
_cell_measurement_theta_min      2.3392
_cell_volume                     1104.9(5)
_computing_cell_refinement       'SAINT (Bruker)'
_computing_data_collection       'SMART (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10607
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.892
_exptl_absorpt_correction_T_max  0.8048
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                3580
_reflns_number_total             4999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02638_si_002.cif
_cod_data_source_block           Compound1g
_cod_original_cell_volume        1104.8(5)
_cod_database_code               4033206