Efficient synthesis of (P-chirogenic) o-boronated phosphines from sec-phosphine boranes.
Bayardon, Jérôme; Bernard, Julie; Rémond, Emmanuelle; Rousselin, Yoann; Malacea-Kabbara, Raluca; Jugé, Sylvain; Organic letters 17 (2015) 1216–1219; doi:10.1021/acs.orglett.5b00167

data_1554802
_publ_section_title
;
 Efficient synthesis of (P-chirogenic) o-boronated phosphines from
 sec-phosphine boranes.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1216
_journal_page_last               1219
_journal_paper_doi               10.1021/acs.orglett.5b00167
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C24 H41 B2 O2 P'
_chemical_formula_sum            'C24 H41 B2 O2 P'
_chemical_formula_weight         414.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.09 svn.r3131 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-01-12 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.60140(10)
_cell_length_b                   17.6656(3)
_cell_length_c                   16.4517(3)
_cell_measurement_temperature    115
_cell_volume                     2388.51(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_orient_matrix_type       'Nonius Collect from scalepack cell'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10374
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.481
_diffrn_reflns_theta_min         2.837
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and methanol by slow evaporation'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0542P)^2^+0.3829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4036
_reflns_number_total             5468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00167_si_002.cif
_cod_data_source_block           08jb247
_cod_database_code               1554802
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H,H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 B1(H1A,H1B,H1C)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C19(H19)
2.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C6(H6A,H6B), C20(H20A,H20B), C23(H23A,H23B), C22(H22A,H22B),
 C4(H4A,H4B), C21(H21A,H21B), C5(H5A,H5B), C2(H2A,H2B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C11(H11)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C18(H18A,H18B,
 H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2008-07-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with grease'
_olex2_submission_original_sample_id 08jb247
_olex2_submission_special_instructions 'No special instructions were received'