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_1554803
_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         'C28 H33 B2 Fe O2 P'
_chemical_formula_sum            'C28 H33 B2 Fe O2 P'
_chemical_formula_weight         509.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-01-13 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 113.497(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.674(2)
_cell_length_b                   9.2986(14)
_cell_length_c                   12.919(2)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.835
_cell_measurement_theta_min      2.784
_cell_volume                     1396.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28533
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.785
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0594 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8727.
The \l/2 correction factor is 0.00150.
;
_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    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and methanol by slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6346
_refine_ls_number_restraints     481
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4950
_reflns_number_total             6346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00167_si_002.cif
_cod_data_source_block           13jb972_295k_0m
_cod_database_code               1554803
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-B1 = O2-B1
 1.37 with sigma of 0.02
 O2-C23 = O1-C24
 1.48 with sigma of 0.02
 C24-C23
 1.58 with sigma of 0.02
 C28-C24 = C27-C24 = C25-C23 = C26-C23
 1.5 with sigma of 0.02
 O2A-B1A = O1A-B1A
 1.37 with sigma of 0.02
 O2A-C23A = O1A-C24A
 1.48 with sigma of 0.02
 C24A-C23A
 1.58 with sigma of 0.02
 C25A-C23A = C26A-C23A = C27A-C24A = C24A-C28A
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O2(0.5) B1(0.5) C23(0.5) O1(0.5) C25(0.5) H25A(0.5) H25B(0.5)
 H25C(0.5) C26(0.5) H26A(0.5) H26B(0.5) H26C(0.5) C24(0.5) C27(0.5) H27A(0.5)
 H27B(0.5) H27C(0.5) C28(0.5) H28A(0.5) H28B(0.5) H28C(0.5) C27A(0.5) H27D(0.5)
 H27E(0.5) H27F(0.5) C24A(0.5) C28A(0.5) H28D(0.5) H28E(0.5) H28F(0.5)
 C23A(0.5) C25A(0.5) H25D(0.5) H25E(0.5) H25F(0.5) C26A(0.5) H26D(0.5)
 H26E(0.5) H26F(0.5) O1A(0.5) O2A(0.5) B1A(0.5)
5.a Riding coordinates:
 B2(H2A,H2B,H2C)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7), C6(H6), C21(H21), C20(H20), C19(H19), C18(H18),
 C3(H3), C2(H2), C1(H1), C5(H5), C4(H4), C16(H16), C15(H15), C14(H14), C13(H13),
  C12(H12)
5.c Fitted pentagon refined as free rotating group:
 C10(C9,C8,C7,C6), C3(C2,C1,C5,C4)
5.d Fitted hexagon refined as free rotating group:
 C22(C21,C20,C19,C18,C17), C11(C16,C15,C14,C13,C12)
5.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C27A(H27D,H27E,H27F), C28A(H28D,H28E,H28F), C25A(H25D,H25E,H25F),
 C26A(H26D,H26E,H26F)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'