Dearomatization Strategy and Palladium-Catalyzed Domino Reaction: Construction of Azepino[5,4,3-cd]indoles from 2-Alkynylanilines.
Zheng, Chen; Chen, Jin Jin; Fan, Renhua; Organic letters 16 (2014) 816–819; doi:10.1021/ol403557q

data_1513468
_publ_section_title
;
 Dearomatization Strategy and Palladium-Catalyzed Domino Reaction:
 Construction of Azepino[5,4,3-cd]indoles from 2-Alkynylanilines.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              816
_journal_page_last               819
_journal_paper_doi               10.1021/ol403557q
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C30 H27 Cl N2 O4 S'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.900(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   10.384(9)
_cell_length_c                   18.902(15)
_cell_measurement_reflns_used    1011
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.292
_cell_measurement_theta_min      2.202
_cell_volume                     2688(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
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_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.025
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             1144
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_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0089(9)
_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   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0706P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3522
_reflns_number_total             5264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403557q_si_002.cif
_cod_data_source_block           a31030a
_cod_database_code               1513468
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.938
_shelxl_version_number           2013-2
_shelx_res_checksum              7680
_shelx_hkl_checksum              74702