Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic Phosphines Based on Aryne Chemistry
Jérôme Bayardon; Hugo Laureano; Vincent Diemer; Mathieu Dutartre; Utpal Das; Yoann Rousselin; Jean-Christophe Henry; Françoise Colobert; Frédéric R. Leroux; Sylvain Jugé; Journal of Organic Chemistry 77 (2012) 5759–5769; doi:10.1021/jo300910w

data_4027282
_publ_contact_author_address
;
ICMUB
UMR 5260
CNRS - Univ. de Bourgogne
9 avenue AlainSavary
21078 Dijon Cedex
France
;
_publ_contact_author_email       Sylvain.Juge@u-bourgogne.fr
_publ_contact_author_fax         '+33 (0)3 80 39 60 98'
_publ_contact_author_name        'Sylvain Juge'
_publ_contact_author_phone       '+33 (0)3 80 39 61 13 '
_publ_section_title
;
 Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic
 Phosphines Based on Aryne Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5759
_journal_page_last               5769
_journal_paper_doi               10.1021/jo300910w
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 B Br Fe P'
_chemical_formula_sum            'C22 H21 B Br Fe P'
_chemical_formula_weight         462.93
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-06-14 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.6280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6961(2)
_cell_length_b                   14.5022(5)
_cell_length_c                   9.1795(3)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     970.85(5)
_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    'ORTEP3 (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4164
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    2.920
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       Prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0273P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                3891
_reflns_number_total             4164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300910w_si_005.cif
_cod_data_source_block           08jb193
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4027282