Anti-Markovnikov hydrophosphoroselenoylation of alkenes using phosphorodiselenoic acid esters leading to the formation of phosphonoselenoic acid esters
Toshiaki Murai; Yuuki Maekawa; Masaki Monzaki; Takafumi Ando; Toshifumi Maruyama; Chem.Commun. 49 (2013) 9675–; doi:10.1039/c3cc45912h

data_7109869
_publ_section_title
;
 Anti-Markovnikov hydrophosphoroselenoylation of alkenes using
 phosphorodiselenoic acid esters leading to the formation of
 phosphonoselenoic acid esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              9675
_journal_paper_doi               10.1039/c3cc45912h
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H21 O3 P Se'
_chemical_formula_sum            'C25 H21 O3 P Se'
_chemical_formula_weight         479.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.479(8)
_cell_length_b                   10.231(5)
_cell_length_c                   12.459(6)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     2228.0(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17803
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(14)
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+2.0810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1711
_reflns_number_gt                4573
_reflns_number_total             5079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45912h.txt
_cod_data_source_block           crystalclear
_cod_original_cell_volume        2227.9(19)
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_database_code               7109869