Stereoselective Synthesis of (E)-3-alkylideneoxindoles via Gold(I)-Catalyzed Cross-Coupling of 3-Diazooxindoles with Diazoesters.
Cheng, Haiyang; Yao, Xinbo; Yin, Shiwei; Wang, Tao; Zhang, Zunting; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00156

data_4038272
_publ_section_title
;
 Stereoselective Synthesis of (E)-3-alkylideneoxindoles via
 Gold(I)-Catalyzed Cross-Coupling of 3-Diazooxindoles with Diazoesters.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00156
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 I N O5'
_chemical_formula_sum            'C22 H20 I N O5'
_chemical_formula_weight         505.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.314(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7031(14)
_cell_length_b                   10.0960(13)
_cell_length_c                   19.634(3)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.324
_cell_measurement_theta_min      4.380
_cell_volume                     2080.4(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      152.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34900
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         4.212
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.379
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1421 before and 0.0826 after correction. The Ratio of minimum to maximum transmission is 0.5135. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.816
_refine_diff_density_min         -1.788
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+3.3045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3795
_reflns_number_total             3796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00156_si_002.cif
_cod_data_source_block           s
_cod_database_code               4038272
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.119
_shelx_estimated_absorpt_t_min   0.063
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00I(H00I), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00C,H00D), C00R(H00F,H00G,H00H), C00S(H00J,H00K,H00M), C00T(H00R,
 H00S,H00T)
;
_shelx_res_checksum              24731
_shelx_hkl_checksum              47219
_olex2_submission_special_instructions 'No special instructions were received'