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_1555959
_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         'C26 H18 Cl N O'
_chemical_formula_sum            'C26 H18 Cl N O'
_chemical_formula_weight         395.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.170(3)
_cell_angle_beta                 100.710(3)
_cell_angle_gamma                95.382(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9082(6)
_cell_length_b                   9.9372(8)
_cell_length_c                   11.1764(8)
_cell_measurement_reflns_used    7844
_cell_measurement_temperature    298(2)
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_cell_measurement_theta_min      2.34
_cell_volume                     967.63(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.1137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.287
_diffrn_reflns_theta_min         2.338
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6303
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_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1769
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0617P)^2^+0.1971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3038
_reflns_number_total             6303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03224_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1555959
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              86325
_shelx_hkl_checksum              29952