Mechanisms of Stereomutation and Thermolysis of Spiro-1,2-oxaphosphetanes: New Insights into the Second Step of the Wittig Reaction
Jesús García López; Antonio Morán Ramallal; Javier González; Laura Roces; Santiago García-Granda; María José Iglesias; Pascual Oña-Burgos; Fernando López Ortiz; Journal of the American Chemical Society 134 (2012) 19504–19507; doi:10.1021/ja307330c

data_4118942
_publ_contact_author_address
;\'Area de Qu\'imica Org\'anica
Universidad de Almer\'ia
04120  Almer\'ia
Spain
;
_publ_contact_author_email       flortiz@ual.es
_publ_contact_author_name        'Fernando L\'opez-Ortiz'
_publ_contact_author_phone       +34950015478
_publ_section_title
;
 Mechanisms of Stereomutation and Thermolysis of
 Spiro-1,2-oxaphosphetanes: New Insights into the Second Step of the
 Wittig Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19504
_journal_page_last               19507
_journal_paper_doi               10.1021/ja307330c
_journal_volume                  134
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H30 N1 O2 P1'
_chemical_formula_sum            'C25 H30 N O2 P'
_chemical_formula_weight         407.47
_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   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 105.241(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.427(4)
_cell_length_b                   11.154(4)
_cell_length_c                   15.751(5)
_cell_measurement_reflns_used    127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.17
_cell_measurement_theta_min      2.49
_cell_measurement_wavelength     0.71073
_cell_volume                     2106.5(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.102
_diffrn_reflns_av_unetI/netI     0.1489
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11433
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.7
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        XABS2
        Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
        Linear fit to sin(theta)/lambda - 12 parameters
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.135
_refine_ls_R_factor_gt           0.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                2360
_reflns_number_total             3851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307330c_si_002_2.cif
_cod_data_source_block           (+-)-6_j85p2m
_cod_original_sg_symbol_Hall     -P2ybc
_cod_database_code               4118942