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_1554804
_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_absolute_configuration ad
_chemical_formula_moiety         'C40 H43 B2 Fe P'
_chemical_formula_sum            'C40 H43 B2 Fe P'
_chemical_formula_weight         632.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-03-13
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.12.05 svn.r2549, GUI svn.r4385)
;
_audit_update_record
;
2013-03-13 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3874(6)
_cell_length_b                   17.4963(10)
_cell_length_c                   18.3521(9)
_cell_measurement_reflns_used    9081
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.3556
_cell_measurement_theta_min      2.2529
_cell_volume                     3335.3(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SHELXS-97, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_diffrn_ambient_temperature      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            136053
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.219
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.010(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         7678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+1.3817P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7316
_reflns_number_total             7678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00167_si_002.cif
_cod_data_source_block           13jb977
_cod_database_code               1554804
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1 of C1, H2 of C2, H4 of C4, H5 of C5, H6 of C6, H7 of C7, H8 of C8, H9 of
  C9, H10 of C10, H11 of C11, H13 of C13, H14 of C14, H15 of C15, H16 of C16,
  H18 of C18, H19 of C19, H20 of C20, H21 of C21, H25 of C25, H27 of C27, H34
  of C34, H36 of C36, H6B of C6B, H7B of C7B, H8B of C8B, H9B of C9B, H10B of
  C10B
 At 1.5 times of:
  {H1A,H1B,H1C} of B1, {H29A,H29B,H29C} of C29, {H30A,H30B,H30C} of C30,
  {H31A,H31B,H31C} of C31, {H38A,H38B,H38C} of C38, {H39A,H39B,H39C} of C39,
  {H40A,H40B,H40C} of C40
2. Uiso/Uaniso restraints and constraints
Uanis(C9B) = Uanis(C8B) = Uanis(C7B) = Uanis(C10B) = Uanis(C6B)
Uanis(C6) = Uanis(C10) = Uanis(C9) = Uanis(C8) = Uanis(C7)
3. Others
 Fixed Sof: C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5)
 C10(0.5) H10(0.5) C6B(0.5) H6B(0.5) C7B(0.5) H7B(0.5) C8B(0.5) H8B(0.5)
 C9B(0.5) H9B(0.5) C10B(0.5) H10B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
  C21(H21), C25(H25), C27(H27), C34(H34), C36(H36), C6B(H6B), C7B(H7B),
 C8B(H8B), C9B(H9B), C10B(H10B)
4.b Fitted pentagon refined as free rotating group:
 C6(C7,C8,C9,C10), C6B(C7B,C8B,C9B,C10B)
4.c Idealised Me refined as rotating group:
 B1(H1A,H1B,H1C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
;
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.837
_shelx_hkl_checksum              91529
_shelx_res_checksum              13869
_shelxl_version_number           2013-2