Copper-Catalyzed Selective N-Vinylation of 3-(Hydroxyimino)indolin-2-ones with Alkenyl Boronic Acids: Synthesis of N-Vinyl Nitrones and Spirooxindoles.
Chen, Chun-Hua; Liu, Qing-Qing; Ma, Xiao-Pan; Feng, Yu; Liang, Cui; Pan, Cheng-Xue; Su, Gui-Fa; Mo, Dong-Liang; The Journal of organic chemistry 82 (2017) 6417–6425; doi:10.1021/acs.joc.7b00620

data_4032755
_publ_section_title
;
 Copper-Catalyzed Selective N-Vinylation of 3-(Hydroxyimino)indolin-2-ones
 with Alkenyl Boronic Acids: Synthesis of N-Vinyl Nitrones and
 Spirooxindoles.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6417
_journal_page_last               6425
_journal_paper_doi               10.1021/acs.joc.7b00620
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C14.88 H14.75 F3 N2 O3'
_chemical_formula_sum            'C14.88 H14.76 F3 N2 O3'
_chemical_formula_weight         326.60
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                87.872(11)
_cell_angle_beta                 87.558(11)
_cell_angle_gamma                83.708(12)
_cell_formula_units_Z            2
_cell_length_a                   5.158(4)
_cell_length_b                   9.565(7)
_cell_length_c                   16.058(11)
_cell_measurement_reflns_used    8312
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.345
_cell_measurement_theta_min      2.585
_cell_volume                     786.3(10)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8427
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.27
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9604
_exptl_crystal_colour            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.358
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.358
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0860
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2952
_refine_ls_wR_factor_ref         0.3103
_reflns_number_gt                2212
_reflns_number_total             2762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00620_si_002.cif
_cod_data_source_block           aaaa
_cod_database_code               4032755
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C8(H8), C9(H9), C11(H11), C13(H13), C17(H17)
3.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC)
;
_olex2_submission_special_instructions 'No special instructions were received'