Regiospecific and stereoselective synthesis of (E)- and (Z)-2-phosphino-1-alkenyl boronates via Cu-catalyzed hydroboration of alkynylphosphines
Song, Liubing; Ma, Xufeng; Xu, Sheng; Shi, Min; Zhang, Jun; New Journal of Chemistry 42 (2018) 8342–; doi:10.1039/C8NJ00892B

data_7057297
_publ_section_title
;
 Regiospecific and stereoselective synthesis of (E)- and
 (Z)-2-phosphino-1-alkenyl boronates via Cu-catalyzed hydroboration of
 alkynylphosphines
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8342
_journal_paper_doi               10.1039/C8NJ00892B
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C26 H34 Au B Cl O2 P'
_chemical_formula_sum            'C26 H34 Au B Cl O2 P'
_chemical_formula_weight         652.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                88.786(3)
_cell_angle_beta                 79.733(3)
_cell_angle_gamma                82.636(3)
_cell_formula_units_Z            6
_cell_length_a                   11.9069(9)
_cell_length_b                   15.0564(10)
_cell_length_c                   22.5926(15)
_cell_measurement_reflns_used    7357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.39
_cell_volume                     3952.6(5)
_computing_cell_refinement       SAINT
_computing_data_collection       'APEX3 BRUKER'
_computing_data_reduction        SADABS
_computing_molecular_graphics    SHELXLE
_computing_publication_material  SHELXTL,BRUKER,2017
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            62240
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.642
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.765
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             1932
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.152
_refine_diff_density_min         -2.567
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     919
_refine_ls_number_reflns         16112
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+15.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13903
_reflns_number_total             16112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj00892b2.cif
_cod_data_source_block           mo_20170612hl2_0m
_cod_depositor_comments
'Adding full bibliography for 7057297--7057299.cif.'
_cod_database_code               7057297
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.392
_shelx_estimated_absorpt_t_min   0.161
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.033) H3(0.046) H4(0.048) H5(0.044) H6(0.034) H8(0.028)
 H9(0.035) H10(0.037) H11(0.038) H12(0.03) H13(0.022) H15(0.021) H16A(0.028)
 H16B(0.028) H17A(0.03) H17B(0.03) H18A(0.034) H18B(0.034) H19A(0.04)
 H19B(0.04) H20A(0.033) H20B(0.033) H22A(0.085) H22B(0.085) H22C(0.085)
 H23A(0.083) H23B(0.083) H23C(0.083) H25A(0.077) H25B(0.077) H25C(0.077)
 H26A(0.1) H26B(0.1) H26C(0.1) H2(0.036) H3(0.043) H4(0.04) H5(0.04) H6(0.031)
 H8(0.025) H9(0.032) H10(0.037) H11(0.038) H12(0.033) H13(0.022) H15(0.02)
 H16A(0.029) H16B(0.029) H17A(0.038) H17B(0.038) H18A(0.04) H18B(0.04)
 H19A(0.032) H19B(0.032) H20A(0.026) H20B(0.026) H22A(0.086) H22B(0.086)
 H22C(0.086) H23A(0.09) H23B(0.09) H23C(0.09) H25A(0.071) H25B(0.071)
 H25C(0.071) H26A(0.085) H26B(0.085) H26C(0.085) H2(0.038) H3(0.046) H4(0.042)
 H5(0.062) H6(0.054) H8(0.031) H9(0.038) H10(0.041) H11(0.04) H12(0.031)
 H13(0.021) H15(0.021) H16A(0.025) H16B(0.025) H17A(0.035) H17B(0.035)
 H18A(0.041) H18B(0.041) H19A(0.035) H19B(0.035) H20A(0.029) H20B(0.029)
 H25A(0.1) H25B(0.1) H25C(0.1) H26A(0.101) H26B(0.101) H26C(0.101) H25D(0.12)
 H25E(0.12) H25F(0.12) H26D(0.108) H26E(0.108) H26F(0.108) H23A(0.107)
 H23B(0.107) H23C(0.107) H24A(0.077) H24B(0.077) H24C(0.077) H23D(0.101)
 H23E(0.101) H23F(0.101) H24D(0.103) H24E(0.103) H24F(0.103)
 Fixed X: H2(0.766745) H3(0.839435) H4(0.925197) H5(0.945364) H6(0.868655)
 H8(0.685306) H9(0.733591) H10(0.849548) H11(0.91917) H12(0.875027)
 H13(0.568017) H15(0.591192) H16A(0.40313) H16B(0.532165) H17A(0.462517)
 H17B(0.358358) H18A(0.532832) H18B(0.404076) H19A(0.438686) H19B(0.34382)
 H20A(0.473481) H20B(0.577025) H22A(0.014797) H22B(0.097525) H22C(0.05832)
 H23A(0.21984) H23B(0.091561) H23C(0.130155) H25A(0.255393) H25B(0.251472)
 H25C(0.137472) H26A(0.245297) H26B(0.209918) H26C(0.119232) H2(0.650452)
 H3(0.586637) H4(0.480047) H5(0.434928) H6(0.495774) H8(0.474481) H9(0.417371)
 H10(0.493529) H11(0.627175) H12(0.682334) H13(0.813008) H15(0.754121)
 H16A(0.986872) H16B(0.888487) H17A(0.925676) H17B(0.797988) H18A(0.876605)
 H18B(0.979212) H19A(0.845272) H19B(0.746334) H20A(0.804448) H20B(0.933076)
 H22A(1.119229) H22B(1.097491) H22C(1.223613) H23A(1.205535) H23B(1.193588)
 H23C(1.298884) H25A(1.314289) H25B(1.196176) H25C(1.269423) H26A(1.216799)
 H26B(1.330288) H26C(1.258223) H2(-0.216054) H3(-0.292124) H4(-0.242575) H5(-
 0.12601) H6(-0.050523) H8(-0.024836) H9(-0.084062) H10(-0.191819) H11(-
 0.245921) H12(-0.190621) H13(0.115522) H15(0.080749) H16A(0.129671)
 H16B(0.259862) H17A(0.181226) H17B(0.082036) H18A(0.220813) H18B(0.317437)
 H19A(0.264093) H19B(0.134898) H20A(0.214587) H20B(0.314955) H25A(0.594618)
 H25B(0.667236) H25C(0.620909) H26A(0.501679) H26B(0.57457) H26C(0.439967)
 H25D(0.503816) H25E(0.627685) H25F(0.557399) H26D(0.659153) H26E(0.561728)
 H26F(0.601315) H23A(0.469726) H23B(0.464616) H23C(0.580253) H24A(0.46884)
 H24B(0.48445) H24C(0.586056) H23D(0.524803) H23E(0.484659) H23F(0.60163)
 H24D(0.541824) H24E(0.418117) H24F(0.433419)
 Fixed Y: H2(0.436322) H3(0.55567) H4(0.538818) H5(0.401678) H6(0.281662)
 H8(0.192578) H9(0.058729) H10(-0.057894) H11(-0.040088) H12(0.095026)
 H13(0.346602) H15(0.156611) H16A(0.099584) H16B(0.080569) H17A(0.226957)
 H17B(0.193793) H18A(0.080501) H18B(0.099619) H19A(-0.04109) H19B(0.022524)
 H20A(-0.046448) H20B(-0.012706) H22A(0.3585) H22B(0.366062) H22C(0.273314)
 H23A(0.233515) H23B(0.278293) H23C(0.194549) H25A(0.368472) H25B(0.470511)
 H25C(0.426085) H26A(0.523134) H26B(0.46471) H26C(0.499054) H2(0.778807)
 H3(0.910078) H4(1.027594) H5(1.014449) H6(0.882851) H8(0.594776) H9(0.467097)
 H10(0.415409) H11(0.490954) H12(0.618883) H13(0.645921) H15(0.837263)
 H16A(0.820585) H16B(0.77851) H17A(0.91111) H17B(0.920268) H18A(1.049686)
 H18B(0.992833) H19A(1.051952) H19B(1.010566) H20A(0.919492) H20B(0.910511)
 H22A(0.543878) H22B(0.646416) H22C(0.597525) H23A(0.553758) H23B(0.489701)
 H23C(0.544196) H25A(0.718851) H25B(0.768642) H25C(0.814274) H26A(0.692677)
 H26B(0.690234) H26C(0.782255) H2(0.723488) H3(0.609858) H4(0.462036)
 H5(0.429189) H6(0.542041) H8(0.803809) H9(0.938715) H10(1.053765)
 H11(1.029286) H12(0.89333) H13(0.649538) H15(0.834537) H16A(0.917784)
 H16B(0.903826) H17A(1.045984) H17B(1.006305) H18A(1.037383) H18B(0.978239)
 H19A(0.896189) H19B(0.910827) H20A(0.767221) H20B(0.806145) H25A(0.716015)
 H25B(0.677511) H25C(0.779784) H26A(0.803569) H26B(0.713547) H26C(0.723725)
 H25D(0.645758) H25E(0.648357) H25F(0.736048) H26D(0.716994) H26E(0.78014)
 H26F(0.803913) H23A(0.602464) H23B(0.508593) H23C(0.550828) H24A(0.493553)
 H24B(0.570818) H24C(0.533372) H23D(0.496564) H23E(0.48089) H23F(0.518355)
 H24D(0.616175) H24E(0.587372) H24F(0.688302)
 Fixed Z: H2(0.815844) H3(0.762936) H4(0.663517) H5(0.617087) H6(0.668391)
 H8(0.680568) H9(0.627806) H10(0.664338) H11(0.751301) H12(0.803265)
 H13(0.763143) H15(0.851028) H16A(0.807434) H16B(0.775513) H17A(0.931098)
 H17B(0.907958) H18A(0.953363) H18B(0.985794) H19A(0.936631) H19B(0.910945)
 H20A(0.830589) H20B(0.854035) H22A(0.829425) H22B(0.875345) H22C(0.864061)
 H23A(0.719437) H23B(0.731957) H23C(0.769305) H25A(0.679306) H25B(0.69318)
 H25C(0.703544) H26A(0.79023) H26B(0.847126) H26C(0.806666) H2(0.660875)
 H3(0.716049) H4(0.675556) H5(0.581663) H6(0.526764) H8(0.531035) H9(0.580418)
 H10(0.663678) H11(0.697263) H12(0.649747) H13(0.562691) H15(0.480538)
 H16A(0.421051) H16B(0.39814) H17A(0.345172) H17B(0.379587) H18A(0.395807)
 H18B(0.419712) H19A(0.50252) H19B(0.479595) H20A(0.555789) H20B(0.522887)
 H22A(0.614727) H22B(0.629985) H22C(0.615004) H23A(0.460931) H23B(0.516697)
 H23C(0.502384) H25A(0.570697) H25B(0.602913) H25C(0.548961) H26A(0.43133)
 H26B(0.457753) H26C(0.447781) H2(0.996702) H3(1.05504) H4(1.0249) H5(0.933181)
 H6(0.87413) H8(0.99257) H9(1.042493) H10(0.998825) H11(0.908021) H12(0.858822)
 H13(0.909782) H15(0.81824) H16A(0.89319) H16B(0.862762) H17A(0.837203)
 H17B(0.813321) H18A(0.731018) H18B(0.758305) H19A(0.683677) H19B(0.715863)
 H20A(0.739408) H20B(0.762635) H25A(0.788083) H25B(0.83642) H25C(0.836455)
 H26A(0.932821) H26B(0.946264) H26C(0.962765) H25D(0.783374) H25E(0.797339)
 H25F(0.777982) H26D(0.886473) H26E(0.926821) H26F(0.859047) H23A(0.785388)
 H23B(0.816417) H23C(0.804796) H24A(0.920656) H24B(0.962749) H24C(0.91192)
 H23D(0.835435) H23E(0.904369) H23F(0.881487) H24D(0.96039) H24E(0.976835)
 H24F(0.964244)
;
_olex2_submission_special_instructions 'No special instructions were received'