Chemical Synthesis of (RP)- and (SP)-[(16)O,(17)O,(18)O]Phosphoenol Pyruvate.
Malová Križková, Petra; Prechelmacher, Susanne; Roller, Alexander; Hammerschmidt, Friedrich; The Journal of organic chemistry 82 (2017) 10310–10318; doi:10.1021/acs.joc.7b01783

data_4032781
_publ_section_title
;
 Chemical Synthesis of (RP)- and (SP)-[(16)O,(17)O,(18)O]Phosphoenol
 Pyruvate.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10310
_journal_page_last               10318
_journal_paper_doi               10.1021/acs.joc.7b01783
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H21 O6 P'
_chemical_formula_sum            'C16 H21 O6 P'
_chemical_formula_weight         340.30
_chemical_name_systematic
;
Ethyl (+-)-2-(((2R*,6R*)-4,4-dimethyl-2-oxido-6-phenyl
-1,3,2-dioxaphosphinan-2-yl)oxy)-acrylate 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2016-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                97.1640(10)
_cell_angle_beta                 94.7880(10)
_cell_angle_gamma                92.485(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5159(2)
_cell_length_b                   8.9376(3)
_cell_length_c                   12.5585(4)
_cell_measurement_reflns_used    8564
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.078
_cell_measurement_theta_min      2.300
_cell_volume                     832.87(4)
_computing_cell_refinement       'APEX2 v2011.2-0'
_computing_data_collection       'APEX2 v2011.2-0'
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20144
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.149
_diffrn_reflns_theta_min         2.300
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0491 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.9245.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.4180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4229
_reflns_number_total             4844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01783_si_002.cif
_cod_data_source_block           pema455_p-1
_cod_depositor_comments          'Adding full bibliography for 4032781.cif.'
_cod_original_cell_volume        832.86(4)
_cod_database_code               4032781
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.962
_shelx_res_checksum              51278
_shelx_hkl_checksum              64932