Multiple Aryne Insertions into Oxindoles: Synthesis of Bioactive 3,3-Diarylated Oxindoles and Dibenzo[b,e]azepin-6-ones.
Samineni, Ramesh; Bandi, Chandramohan Reddy C.; Srihari, Pabbaraja; Mehta, Goverdhan; Organic letters 18 (2016) 6184–6187; doi:10.1021/acs.orglett.6b03224

data_1555960
_publ_section_title
;
 Multiple Aryne Insertions into Oxindoles: Synthesis of Bioactive
 3,3-Diarylated Oxindoles and Dibenzo[b,e]azepin-6-ones.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6184
_journal_page_last               6187
_journal_paper_doi               10.1021/acs.orglett.6b03224
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H21 N3 O2'
_chemical_formula_sum            'C21 H21 N3 O2'
_chemical_formula_weight         347.41
_chemical_name_systematic
(E)-11-(2-(4-methylpiperazin-1-yl)-2-oxoethylidene)-5,11-dihydro-6H-dibenzo[b,e]azepin-6-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.049(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.510(2)
_cell_length_b                   12.408(3)
_cell_length_c                   8.644(2)
_cell_measurement_reflns_used    7312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.36
_cell_volume                     912.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_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  0.0195
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10651
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.0617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4138
_reflns_number_total             4285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03224_si_002.cif
_cod_data_source_block           BD77M
_cod_original_cell_volume        912.9(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555960
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.977
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              3861
_shelx_hkl_checksum              7145