Synthesis of P-stereogenic diarylphosphinic amides by directed lithiation: transformation into tertiary phosphine oxides via methanolysis, aryne chemistry and complexation behaviour toward zinc(ii).
Del Águila-Sánchez, Miguel A; Navarro, Yolanda; García López, Jesús; Guedes, Guilherme P.; López Ortiz, Fernando; Dalton transactions (Cambridge, England : 2003) 45 (2016) 2008–2022; doi:10.1039/c5dt02860d

data_7036299
_publ_section_title
;
 Synthesis of P-stereogenic diarylphosphinic amides by directed
 lithiation: transformation into tertiary phosphine oxides via
 methanolysis, aryne chemistry and complexation behaviour toward zinc(ii).
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2008
_journal_page_last               2022
_journal_paper_doi               10.1039/c5dt02860d
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H32 N O P Sn'
_chemical_formula_sum            'C21 H32 N O P Sn'
_chemical_formula_weight         464.16
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      96
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-08-20T15:35:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3648(2)
_cell_length_b                   9.3648(2)
_cell_length_c                   51.2257(12)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.99
_cell_measurement_theta_min      3.45
_cell_volume                     4492.47(17)
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_computing_molecular_graphics
'Ortep for Windows(Farrugia,2012)and Mercury (Macrae, 2008).'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1292
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            13912
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        58.986
_diffrn_reflns_theta_max         58.986
_diffrn_reflns_theta_min         3.451
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.77
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate:hexane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.125
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 1147 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+8.9613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.608
_reflns_friedel_fraction_full    1
_reflns_friedel_fraction_max     1
_reflns_number_gt                3196
_reflns_number_total             3243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt02860d1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7036296--7036299.cif.'
_cod_original_cell_volume        4492.5(2)
_cod_database_code               7036299