The Question of Electrophilic vs Nucleophilic Addition of Cyclic β-Dicarbonyl Phenyliodonium Ylides: Electrophilic Cycloaddition of Diphenylketene
Anna Antos; Yiannis Elemes; Adonis Michaelides; John, A. Nyxas; Stavroula Skoulika; Lazaros P. Hadjiarapoglou; Journal of Organic Chemistry 77 (2012) 10949–10954; doi:10.1021/jo3020787

data_4027766
_publ_section_title
;
 The Question of Electrophilic vs Nucleophilic Addition of Cyclic
 \b-Dicarbonyl Phenyliodonium Ylides: Electrophilic Cycloaddition of
 Diphenylketene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10949
_journal_page_last               10954
_journal_paper_doi               10.1021/jo3020787
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H16 O3'
_chemical_formula_weight         304.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.183(2)
_cell_length_b                   10.8970(10)
_cell_length_c                   18.656(3)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.2
_cell_measurement_theta_min      9.2
_cell_volume                     3157.1(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  P4
_diffrn_measurement_method       scintillation
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5659
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5467
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1740
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.6392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                2436
_reflns_number_total             5467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3020787_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4027766