A bio-inspired synthesis of oxindoles by catalytic aerobic dual C‒H functionalization of phenols
Huang, Zheng; Askari, Mohammad S.; Esguerra, Kenneth Virgel N.; Dai, Tian-Yang; Kwon, Ohhyeon; Ottenwaelder, Xavier; Lumb, Jean-Philip; Chem. Sci. 7 (2016) 358–; doi:10.1039/C5SC02395E

data_1534130
_publ_section_title
;
 A bio-inspired synthesis of oxindoles by catalytic aerobic dual C--H
 functionalization of phenols
;
_journal_issue                   1
_journal_name_full               'Chem. Sci.'
_journal_page_first              358
_journal_paper_doi               10.1039/C5SC02395E
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety
'2(C26 H37 Cu N3 O3), 2(F6 Sb), 2.5(C H2 Cl2)'
_chemical_formula_sum            'C54.5 H79 Cl5 Cu2 F12 N6 O6 Sb2'
_chemical_formula_weight         1690.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-09-02 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                79.735(4)
_cell_angle_beta                 89.183(4)
_cell_angle_gamma                63.926(4)
_cell_formula_units_Z            2
_cell_length_a                   13.668(6)
_cell_length_b                   15.095(6)
_cell_length_c                   19.109(8)
_cell_measurement_reflns_used    5975
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.61
_cell_volume                     3475(3)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_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  0.0827
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37455
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         1.086
_exptl_absorpt_coefficient_mu    1.646
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' SADABS-2014/2 - Bruker AXS'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       needle
_exptl_crystal_F_000             1698
_exptl_crystal_size_max          0.794
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.072
_refine_diff_density_max         1.267
_refine_diff_density_min         -1.275
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     847
_refine_ls_number_reflns         15600
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.1088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8633
_reflns_number_total             15600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02395e3.cif
_cod_data_source_block           mo_Mo38_0m
_cod_depositor_comments
'Adding full bibliography for 1534126--1534130.cif.'
_cod_original_cell_volume        3475(2)
_cod_original_formula_sum        'C54.50 H79 Cl5 Cu2 F12 N6 O6 Sb2'
_cod_database_code               1534130
_shelx_estimated_absorpt_t_min   0.355
_shelx_estimated_absorpt_t_max   0.891
_shelxl_version_number           2014-3
_shelx_res_checksum              66153
_shelx_hkl_checksum              79558