[3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones.
Zhang, Kaifan; Xu, Xiaoying; Zheng, Jiuan; Yao, Hequan; Huang, Yue; Lin, Aijun; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00914

data_1546010
_publ_section_title
;
 [3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with
 2-Alkenylindoles: An Approach to Tetrahydro-\b-carbolinones.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00914
_journal_year                    2017
_chemical_formula_sum            'C25 H27 Br N2 O4'
_chemical_formula_weight         499.39
_space_group_crystal_system      monoclinic
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_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
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   9.374(3)
_cell_length_c                   19.421(7)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.097
_cell_measurement_theta_min      2.313
_cell_volume                     2365.8(14)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker smart CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
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_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.884
_diffrn_reflns_theta_min         1.567
_exptl_absorpt_coefficient_mu    1.771
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0036(6)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.2898P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3305
_reflns_number_total             4691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00914_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        2365.9(15)
_cod_database_code               1546010
_shelx_estimated_absorpt_t_min   0.777
_shelx_estimated_absorpt_t_max   0.843
_shelxl_version_number           2013-2
_shelx_res_checksum              82319
_shelx_hkl_checksum              74631