Vinylogous Reactivity of Oxindoles Bearing Nonsymmetric 3-Alkylidene Groups.
Di Iorio, Nicola; Righi, Paolo; Ranieri, Silvia; Mazzanti, Andrea; Margutta, Riccardo G.; Bencivenni, Giorgio; The Journal of organic chemistry 80 (2015) 7158–7171; doi:10.1021/acs.joc.5b01022

data_4031159
_publ_contact_author
;
Prof. Dr. Andrea Mazzanti
University of Bologna
Department of Industrial Chemistry "Toso Montanari"
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_section_title
;
 Vinylogous Reactivity of Oxindoles Bearing Nonsymmetric 3-Alkylidene
 Groups.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7158
_journal_page_last               7171
_journal_paper_doi               10.1021/acs.joc.5b01022
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H24 Br N2 O5.5'
_chemical_formula_weight         496.35
_chemical_name_common            'Compound 5bh'
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             09/06/2013
_audit_creation_method           SHELXL-97
_audit_update_record             07/22/2014
_cell_angle_alpha                90.00
_cell_angle_beta                 121.3460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.584(2)
_cell_length_b                   12.3431(19)
_cell_length_c                   13.574(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2229.9(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12500
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  0.7654
_exptl_absorpt_correction_T_min  0.5196
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.7594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                4363
_reflns_number_total             4821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01022_si_002.cif
_cod_data_source_block           oxaindolo-bromo
_cod_depositor_comments          'Adding full bibliography for 4031159.cif.'
_cod_original_cell_volume        2229.8(6)
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C23 H24 Br N2 O5.50'
_cod_database_code               4031159