Formal [3+3] cycloaddition of indol-2-yl carbinol with azadiene and the oxidative ring expansion reaction for the synthesis of indole azepinones
Xue Zhong; You Li; Jing Zhang; Wu-Xia Zhang; Shi-Xue Wang; Fu-She Han; Chem.Commun. 50 (2014) 11181–; doi:10.1039/C4cc04995K

data_7115643
_publ_section_title
;
 Formal [3+3] cycloaddition of indol-2-yl carbinol with azadiene and the
 oxidative ring expansion reaction for the synthesis of indole azepinones
;
_journal_name_full               Chem.Commun.
_journal_page_first              11181
_journal_paper_doi               10.1039/C4cc04995K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.579(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3854(18)
_cell_length_b                   18.319(3)
_cell_length_c                   11.434(2)
_cell_measurement_reflns_used    3268
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.19
_cell_volume                     1852.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      187(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX 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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10721
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0587P)^2^+0.1275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                2136
_reflns_number_total             3268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc04995k2.cif
_cod_data_source_block           x161
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7115643