Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates.
Gnawali, Giri Raj; Rath, Nigam P.; Spilling, Christopher D.; The Journal of organic chemistry 84 (2019) 8724–8730; doi:10.1021/acs.joc.9b00905

data_4034136
_publ_section_title
;
 Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy
 Vinyl Phosphonates.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8724
_journal_page_last               8730
_journal_paper_doi               10.1021/acs.joc.9b00905
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H29 O4 P'
_chemical_formula_sum            'C18 H29 O4 P'
_chemical_formula_weight         340.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 91.135(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.6012(17)
_cell_length_b                   10.1533(10)
_cell_length_c                   9.6226(7)
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.26
_cell_volume                     1914.7(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      199(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12735
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.740
_diffrn_reflns_theta_min         2.078
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+0.9793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2251
_reflns_number_total             3642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00905_si_002.cif
_cod_data_source_block           s17717
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034136
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              98077
_shelx_hkl_checksum              47151