Catalytic asymmetric hydrophosphinylation of alpha,beta-unsaturated N-acylpyrroles: application of dialkyl phosphine oxides in enantioselective synthesis of chiral phosphine oxides or phosphines.
Zhao, Depeng; Mao, Lijuan; Wang, Yuan; Yang, Dongxu; Zhang, Quanliang; Wang, Rui; Organic letters 12 (2010) 1880–1882; doi:10.1021/ol100504h

data_1502942
_publ_section_title
;
 Catalytic asymmetric hydrophosphinylation of alpha,beta-unsaturated
 N-acylpyrroles: application of dialkyl phosphine oxides in
 enantioselective synthesis of chiral phosphine oxides or phosphines.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1880
_journal_page_last               1882
_journal_paper_doi               10.1021/ol100504h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C17 H21 Br N O2 P'
_chemical_formula_weight         382.23
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.141(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4412(10)
_cell_length_b                   18.481(3)
_cell_length_c                   9.1796(16)
_cell_measurement_reflns_used    1065
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.95
_cell_measurement_theta_min      2.56
_cell_volume                     886.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4810
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.5411
_exptl_absorpt_correction_T_min  0.4606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                1784
_reflns_number_total             2468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100504h_si_002.cif
_cod_data_source_block           p21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502942