Mechanistic Aspects of the Phosphine-Catalyzed Isomerization of Allenic Sulfones to 2-Arylsulfonyl 1,3-Dienes.
Hampton, Carissa S.; Harmata, Michael; The Journal of organic chemistry 80 (2015) 12151–12158; doi:10.1021/acs.joc.5b02097

data_4031740
_publ_section_title
;
 Mechanistic Aspects of the Phosphine-Catalyzed Isomerization of Allenic
 Sulfones to 2-Arylsulfonyl 1,3-Dienes.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12151
_journal_page_last               12158
_journal_paper_doi               10.1021/acs.joc.5b02097
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C30 H30 O2 P1 S1, P F6'
_chemical_formula_sum            'C30 H30 F6 O2 P2 S'
_chemical_formula_weight         630.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9685(3)
_cell_length_b                   18.6756(3)
_cell_length_c                   20.5316(3)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      4.3
_cell_volume                     5739.52(17)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            56706
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.173
_diffrn_reflns_theta_min         4.307
_diffrn_source                   'Incoatec Cu microfocus tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 G\"ottingen, Germany).
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+3.9323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5251
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02097_si_002.cif
_cod_data_source_block           CCS-HXI-116
_cod_depositor_comments          'Adding full bibliography for 4031740.cif.'
_cod_original_formula_sum        'C30 H30 F6 O2 P2 S1'
_cod_database_code               4031740
_shelx_estimated_absorpt_t_min   0.619
_shelx_estimated_absorpt_t_max   0.857
_shelxl_version_number           2013-4
_shelx_res_checksum              5220
_shelx_hkl_checksum              939