Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P-C bond formation and hydrogenation.
Badkar, Pallavi A.; Rath, Nigam P.; Spilling, Christopher D.; Organic letters 9 (2007) 3619–3622; doi:10.1021/ol701500s

data_1505509
_publ_section_title
;
 Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P-C bond
 formation and hydrogenation.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3619
_journal_page_last               3622
_journal_paper_doi               10.1021/ol701500s
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C10 H10 Br O5 P'
_chemical_formula_weight         321.06
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.758(2)
_cell_angle_beta                 82.910(2)
_cell_angle_gamma                85.120(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1046(2)
_cell_length_b                   7.8696(3)
_cell_length_c                   10.7309(3)
_cell_measurement_reflns_used    6750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     561.49(3)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2005)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29966
_diffrn_reflns_theta_full        37.49
_diffrn_reflns_theta_max         37.49
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    3.809
_exptl_absorpt_correction_T_max  0.8196
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'sadabs v2006/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         5888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0365
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0621
_reflns_number_gt                5004
_reflns_number_total             5888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701500s-file001.cif
_cod_data_source_block           s5306
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505509