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_7115641
_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 O5'
_chemical_formula_weight         370.40
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_symmetry_space_group_name_Hall  '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.2330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2319(11)
_cell_length_b                   7.8737(6)
_cell_length_c                   15.4675(11)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.63
_cell_volume                     1855.0(2)
_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      188(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
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_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0614P)^2^+0.4868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                3037
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc04995k2.cif
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