Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
Moglie, Yanina; González-Soria, María José; Martín-García, Iris; Radivoy, Gabriel; Alonso, Francisco; Green Chem. 18 (2016) 4896–; doi:10.1039/C6GC00903D

data_7226726
_publ_section_title
;
 Catalyst- and solvent-free hydrophosphination and multicomponent
 hydrothiophosphination of alkenes and alkynes
;
_journal_issue                   18
_journal_name_full               'Green Chem.'
_journal_page_first              4896
_journal_paper_doi               10.1039/C6GC00903D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 P S'
_chemical_formula_sum            'C20 H17 P S'
_chemical_formula_weight         320.37
_chemical_melting_point          377.5(5)
_chemical_name_systematic        '(Z)-Diphenyl(styryl)phosphine sulfide'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.960(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.697(3)
_cell_length_b                   6.6112(11)
_cell_length_c                   17.826(3)
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.3
_cell_volume                     1719.3(5)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13993
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane-ethyl acetate'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.3423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2399
_reflns_number_total             3025
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c6gc00903d2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '377.0--378.0 ' was changed to
'377.5(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7226726