Synthesis of 2,3-Dialkylated Tartaric Acid Esters via Visible Light Photoredox-Catalyzed Reductive Dimerization of α-Ketoesters.
Zhu, Jing; Yuan, Yi; Wang, Shaozhong; Yao, Zhu-Jun; ACS omega 2 (2017) 4665–4677; doi:10.1021/acsomega.7b00749

data_4516902
_publ_section_title
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 Synthesis of 2,3-Dialkylated Tartaric Acid Esters via Visible Light
 Photoredox-Catalyzed Reductive Dimerization of \a-Ketoesters.
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_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              4665
_journal_page_last               4677
_journal_paper_doi               10.1021/acsomega.7b00749
_journal_volume                  2
_journal_year                    2017
_chemical_formula_sum            'C18 H30 O6'
_chemical_formula_weight         342.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 124.978(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.370(2)
_cell_length_b                   16.668(4)
_cell_length_c                   13.0761(18)
_cell_measurement_reflns_used    4130
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.26
_cell_volume                     1851.9(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Apex Smart 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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10108
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0877P)^2^+0.8524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.2120
_reflns_number_gt                2283
_reflns_number_total             4130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00749_si_002.cif
_cod_data_source_block           111111
_cod_original_cell_volume        1851.9(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4516902