Synthesis of <i>S</i>-Alkyl Phosphinocarbodithioates with Switch between P(III) and P(V) Derivatives.
Karpus, Andrii; Daran, Jean-Claude; Poli, Rinaldo; Mazières, Stéphane; Destarac, Mathias A.; Manoury, Eric; The Journal of organic chemistry 84 (2019) 9446–9453; doi:10.1021/acs.joc.9b00590

data_4034398
_publ_section_title
;
 Synthesis of <i>S</i>-Alkyl Phosphinocarbodithioates with Switch between
 P(III) and P(V) Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9446
_journal_page_last               9453
_journal_paper_doi               10.1021/acs.joc.9b00590
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C17 H27 P S2 Se'
_chemical_formula_weight         405.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.660(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6056(3)
_cell_length_b                   11.6865(4)
_cell_length_c                   11.2799(4)
_cell_measurement_reflns_used    8005
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      2.54
_cell_volume                     981.90(6)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXt (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius CAD4 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.699
_diffrn_reflns_theta_min         1.843
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       flattened
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.504(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         5380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.2874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4881
_reflns_number_total             5380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00590_si_001.cif
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034398
_shelx_res_checksum              80867
_shelx_hkl_checksum              73018