Anomalous Reaction of Rh~2~(OAc)~4~-Generated Transient Carbonyl Ylides: Chemoselective Synthesis of Epoxy-Bridged Tetrahydropyranone, Oxepanone, Oxocinone, and Oxoninone Ring Systems
Sengodagounder Muthusamy; Janagiraman Krishnamurthi; Srinivasarao Arulananda Babu; Eringathodi Suresh; Journal of Organic Chemistry 72 (2007) 1252–1262; doi:10.1021/jo0621726

data_4022688
_publ_section_title
;
 Anomalous Reaction of Rh~2~(OAc)~4~-Generated Transient Carbonyl
 Ylides: Chemoselective Synthesis of Epoxy-Bridged Tetrahydropyranone,
 Oxepanone, Oxocinone, and Oxoninone Ring Systems
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1252
_journal_page_last               1262
_journal_paper_doi               10.1021/jo0621726
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C25 H24 O3'
_chemical_formula_weight         372.44
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   40.222(16)
_cell_length_b                   18.798(7)
_cell_length_c                   10.308(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      7
_cell_volume                     7794(6)
_computing_cell_refinement       CAD4-PC
_computing_data_collection       CAD4-PC
_computing_data_reduction        NRCVAX
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.256
_diffrn_measured_fraction_theta_max 0.256
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 Diffractometer'
_diffrn_measurement_method       'Omega-Two Theta Scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.1103
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3395
_diffrn_reflns_theta_full        24.93
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        NIL
_diffrn_standards_interval_time  1H
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2612
_reflns_number_gt                991
_reflns_number_total             1818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0621726si20061204_112319.cif
_cod_data_source_block           014mutu
_cod_depositor_comments
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The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4022688