Aspects of phosphaallene chemistry - heat induced formation of 1,2-dihydrophosphetes by intramolecular nucleophilic aromatic substitution and photochemical generation of tricyclic phosphiranes.
Tendyck, Jonas C.; Klöcker, Hans; Schürmann, Lina; Würthwein, Ernst-Ulrich; Hepp, Alexander; Layh, Marcus; Uhl, Werner; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03056

data_4037964
_publ_section_title
;
 Aspects of phosphaallene chemistry - heat induced formation of
 1,2-dihydrophosphetes by intramolecular nucleophilic aromatic
 substitution and photochemical generation of tricyclic phosphiranes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03056
_journal_year                    2020
_chemical_formula_sum            'C25 H31 O5 P W'
_chemical_formula_weight         626.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8256(14)
_cell_length_b                   12.8053(16)
_cell_length_c                   19.320(3)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      29.930
_cell_measurement_theta_min      2.464
_cell_volume                     2678.2(6)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39875
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.170
_diffrn_reflns_theta_min         2.156
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    4.403
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.094
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 2622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         7879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6754
_reflns_number_total             7879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03056_si_001.cif
_cod_data_source_block           sadp212121_a
_cod_database_code               4037964
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.473
_shelx_estimated_absorpt_t_max   0.810
_shelx_res_checksum              95351
_shelx_hkl_checksum              50126