Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles
Liu, Xiong-Li; Yue, Jing; Chen, Shuang; Liu, Huan-Huan; Yang, Kai-Mo; Feng, Ting-Ting; Zhou, Ying; Organic Chemistry Frontiers 6 (2019) 256–; doi:10.1039/C8QO01222A

data_1554550
_publ_section_title
;
 Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles:
 rapid access to 3-functionalized-2-oxindoles
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              256
_journal_paper_doi               10.1039/C8QO01222A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C19 H19 Cl2 N O4'
_chemical_formula_sum            'C19 H19 Cl2 N O4'
_chemical_formula_weight         396.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-04 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.506(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.580(5)
_cell_length_b                   13.960(2)
_cell_length_c                   8.0737(13)
_cell_measurement_reflns_used    6225
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.36
_cell_volume                     3721.3(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.1026
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.569
_diffrn_reflns_theta_min         1.233
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_exptl_transmission_factor_max   0.4334
_exptl_transmission_factor_min   0.3773
_refine_diff_density_max         1.801
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1235P)^2^+24.7188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2570
_refine_ls_wR_factor_ref         0.2749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3518
_reflns_number_total             4742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01222a2.cif
_cod_data_source_block           mo_gd_lxl40_0m
_cod_original_cell_volume        3721.4(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1554550
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.780
_shelx_estimated_absorpt_t_max   0.906
_shelx_res_checksum              53915
_shelx_hkl_checksum              40896