Addition of optically pure H-phosphinate to ketones: selectivity, stereochemistry and mechanism.
Sun, Yong-Ming; Xin, Nana; Xu, Zhong-Yuan; Liu, Li-Juan; Meng, Fan-Jie; Zhang, He; Fu, Bao-Ci; Liang, Qiu-Ju; Zheng, Hong-Xing; Sun, Li-Jun; Zhao, Chang-Qiu; Han, Li-Biao; Organic & biomolecular chemistry 12 (2014) 9457–; doi:10.1039/c4ob01574f

data_7154155
_publ_section_title
;
 Addition of optically pure H-phosphinate to ketones: selectivity,
 stereochemistry and mechanism.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9457
_journal_paper_doi               10.1039/c4ob01574f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C20 H24 Br O3 P'
_chemical_formula_weight         423.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.362(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4511(12)
_cell_length_b                   19.5742(6)
_cell_length_c                   11.0005(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1998.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7242
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_T_max  0.6728
_exptl_absorpt_correction_T_min  0.4126
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1051P)^2^+5.1791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2647
_reflns_number_gt                1757
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01574f2.cif
_cod_data_source_block           130319g
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7154151--7154157.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7154155