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_4118941
_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_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H10 N1 O2 P1'
_chemical_formula_sum            'C13 H10 N O2 P'
_chemical_formula_weight         243.19
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.942(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.825(3)
_cell_length_b                   8.4463(15)
_cell_length_c                   8.3432(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1174.3(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.1049
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3104
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.1265
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        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    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.692
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1732
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0727P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.146
_reflns_number_gt                1425
_reflns_number_total             1732
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307330c_si_002_1.cif
_cod_data_source_block           s12_j12_2m
_cod_database_code               4118941