Hypervalent iodine-mediated oxidative cyclisation of p-hydroxy acetanilides to 1,2-dispirodienones
Laurent Chabaud; Tatiana Hromjakova; Matt Rambla; Pascal Retailleau; Catherine Guillou; Chem.Commun. 49 (2013) 11542–; doi:10.1039/c3cc47171c

data_7110102
_publ_section_title
;
 Hypervalent iodine-mediated oxidative cyclisation of p-hydroxy
 acetanilides to 1,2-dispirodienones
;
_journal_name_full               Chem.Commun.
_journal_page_first              11542
_journal_paper_doi               10.1039/c3cc47171c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.444(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.86900(10)
_cell_length_b                   15.2039(2)
_cell_length_c                   21.8583(15)
_cell_measurement_reflns_used    2849
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.7
_cell_measurement_theta_min      6.6
_cell_volume                     2942.1(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details
;
scan:
Number of images: 36
Slice: 20.0000 - 200.0000
Image width: 5.0000
Exp time: 240.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 270.0000
XTD: 127.4000
2theta: 0.0000
scan:
Number of images: 20
Slice: 20.0000 - 120.0000
Image width: 5.0000
Exp time: 240.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 90.0000
XTD: 127.4000
2theta: 0.0000
scan:
Number of images: 6
Slice: 40.0000 - 70.0000
Image width: 5.0000
Exp time: 240.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 127.4000
2theta: 0.0000
scan:
Number of images: 6
Slice: 60.0000 - 90.0000
Image width: 5.0000
Exp time: 240.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 30.0000
Phi: 0.0000
XTD: 127.4000
2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.017570
_diffrn_orient_matrix_UB_12      -0.059033
_diffrn_orient_matrix_UB_13      -0.019360
_diffrn_orient_matrix_UB_21      0.111308
_diffrn_orient_matrix_UB_22      -0.011179
_diffrn_orient_matrix_UB_23      0.002588
_diffrn_orient_matrix_UB_31      -0.007704
_diffrn_orient_matrix_UB_32      -0.026877
_diffrn_orient_matrix_UB_33      0.041446
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12944
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         6.63
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00100(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0684P)^2^+1.7292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1920
_reflns_number_gt                3004
_reflns_number_total             5084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47171c.txt
_cod_data_source_block           LC573
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7110102