PIFA-mediated oxidative cyclization of 1-carbamoyl-1-oximylcycloalkanes: synthesis of spiro-fused pyrazolin-5-one N-oxides.
Wang, Kewei; Fu, Xiaolan; Liu, Jinying; Liang, Yongjiu; Dong, Dewen; Organic letters 11 (2009) 1015–1018; doi:10.1021/ol802952e

data_1503798
_publ_section_title
;
 PIFA-mediated oxidative cyclization of 1-carbamoyl-1-oximylcycloalkanes:
 synthesis of spiro-fused pyrazolin-5-one N-oxides.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1015
_journal_page_last               1018
_journal_paper_doi               10.1021/ol802952e
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C15 H18 N2 O2'
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.725(3)
_cell_length_b                   13.381(3)
_cell_length_c                   17.617(4)
_cell_measurement_reflns_used    2678
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.9
_cell_volume                     2764.0(11)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14254
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2678
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.0987
_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^)+(0.0325P)^2^+2.7696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.2009
_reflns_number_gt                1363
_reflns_number_total             2678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802952e_si_001.cif
_cod_data_source_block           aa
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1503798