Syntheses, Structures, and Thermolyses of Pentacoordinate 1,2-Oxastibetanes: Potential Intermediates in the Reactions of Stibonium Ylides with Carbonyl Compounds
Yosuke Uchiyama; Naokazu Kano; Takayuki Kawashima; Journal of Organic Chemistry 71 (2006) 659–670; doi:10.1021/jo0520700

data_4021412
_publ_contact_author_address
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
_publ_contact_author_email       takayuki@chem.s.u-tokyo.ac.jp
_publ_contact_author_fax         +81-5800-6899
_publ_contact_author_name        'Takayuki Kawashima'
_publ_contact_author_phone       +81-5800-6899
_publ_section_title
;
 Syntheses, Structures, and Thermolyses of Pentacoordinate
 1,2-Oxastibetanes: Potential Intermediates in the
 Reactions of Stibonium Ylides with Carbonyl Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              659
_journal_page_last               670
_journal_paper_doi               10.1021/jo0520700
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C34 H28 F9 O2 Sb'
_chemical_formula_sum            'C34 H28 F9 O2 Sb'
_chemical_formula_weight         761.31
_chemical_melting_point          189.5(5)
_chemical_name_common            3-phenyl-1,2-oxastibetane
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 98.600(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.148(3)
_cell_length_b                   9.7367(15)
_cell_length_c                   36.418(7)
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0222
_cell_volume                     6362.6(18)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997-2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.6199
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 17.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 55.0161
              2theta: 24.7780
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 17.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 55.0161
              2theta: 24.7780
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 17.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 55.0161
              2theta: 24.7780

;
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3-circle
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            30621
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_T_max  0.9540
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998) Private communication
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             3040
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.784
_refine_diff_density_min         -1.717
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.427
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.427
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0960
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+133.2111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1799
_reflns_number_gt                6949
_reflns_number_total             7271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0520700si20051003_111008.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '189-190' was changed to '189.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4021412