CAN-Mediated Highly Regio- and Stereoselective Oxidation of Vinylidenecyclopropanes: A Novel Method for the Synthesis of Unsymmetrical Divinyl Ketone and Functional Enone Derivatives
Chenliang Su; Xian Huang; Qingyang Liu; Journal of Organic Chemistry 73 (2008) 6421–6424; doi:10.1021/jo800829a

data_4023601
_publ_section_title
;
 CAN-Mediated Highly Regio- and Stereoselective Oxidation of
 Vinylidenecyclopropanes: A Novel Method for the Synthesis of
 Unsymmetrical Divinyl Ketone and Functional Enone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6421
_journal_page_last               6424
_journal_paper_doi               10.1021/jo800829a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C28 H28 N4 O5'
_chemical_formula_weight         500.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                103.655(3)
_cell_angle_beta                 98.201(3)
_cell_angle_gamma                107.701(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3847(10)
_cell_length_b                   11.1611(14)
_cell_length_c                   14.8806(18)
_cell_measurement_reflns_used    582
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.306
_cell_measurement_theta_min      5.317
_cell_volume                     1254.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0878
_diffrn_reflns_av_sigmaI/netI    0.1731
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6664
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86677
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.109
_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   0.854
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1088P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.2479
_reflns_number_gt                1867
_reflns_number_total             4594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800829a-file001.cif
_cod_data_source_block           cd2820
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023601